Luminescence device and display apparatus

ABSTRACT

In a luminescence device formed of one or plural layers of organic film between a cathode and an anode, at least one layer is a luminescence layer, and a luminescence molecule of a metal coordination compound having a basic structure represented by formula (1) below and having a substituent on at least one of cyclic groups A and B is incorporated as a guest in a host material at a concentration of at least 8 wt. %, which is higher than a concentration at which a luminescence molecule of a similar structure but having no substituent exhibits a maximum luminescence efficiency to form the luminescence layer. As a result, a high-efficiency luminescence device is provided, which is less liable to cause concentration extinction even when a luminescence molecule is contained at a high concentration relative to the host material in the luminescence layer.

TECHNICAL FIELD

[0001] The present invention relates to an organic film luminescencedevice for use in a planar light source, a planar display, etc.

[0002] The present invention relates to a luminescence device using anorganic compound, more particularly to a high-efficiency luminescencedevice containing in its luminescence layer a luminescence materialcomprising a metal coordination compound less liable to causeconcentration extinction even when used at a high concentration.

BACKGROUND ART

[0003] An old example of organic luminescence device is, e.g., one usingluminescence of a vacuum-deposited anthracene film (Thin Solid Films, 94(1982) 171). In recent years, however, in view of advantages, such aseasiness of providing a large-area device compared with an inorganicluminescence device, and possibility of realizing desired luminescencecolors by development of various new materials and drivability at lowvoltages, an extensive study thereon for device formation as aluminescence device of a high-speed responsiveness and a highefficiency, has been conducted.

[0004] As described in detail in, e.g., Macromol. Symp. 125, 1 -48(1997), an organic EL device generally has a structure comprising upperand lower two electrodes and a plurality of organic film layers betweenthe electrodes formed on a transparent substrate. Basic structuresthereof are shown in FIG. 1(a) and (b).

[0005] As shown in FIG. 1, an organic EL device generally has astructure comprising a transparent, electrode 14, a metal electrode 11,and a plurality of organic film layers therebetween on a transparentsubstrate 15.

[0006] In the device of FIG. 1(a), the organic layers comprise aluminescence layer 12 and a hole-transporting layer 13. For thetransparent electrode 14, ITO, etc., having a large work function areused, for providing a good hole-injection characteristic from thetransparent electrode 14 to the hole-transporting layer 13. For themetal electrode 11, a metal, such as aluminum, magnesium or an alloy ofthese, having a small work function is used for providing a goodelectron-injection characteristic. These electrodes have a thickness of50 -200 nm.

[0007] For the luminescence layer 12, aluminum guinolynol complexes (arepresentative example thereof is Alq3 shown hereinafter), etc., havingan electron-transporting characteristic and luminescence characteristicare used. For the hole-transporting layer, biphenyldiamine derivatives(a representative example thereof is α-NPD shown hereinafter), etc.,having an electron-donative characteristic are used.

[0008] The above-structured device has a rectifying characteristic, andwhen an electric field is applied between the metal electrode 11 as acathode and the transparent electrode 14 as an anode, electrons areinjected from the metal electrode 11 into the luminescence layer 12 andholes are injected from the transparent electrode 15. The injected holesand electrons are recombined within the luminescence layer 12 to formexcitons and cause luminescence. At this time, the hole-transportinglayer 13 functions as an electron-blocking layer to increase therecombination efficiency at a boundary between the luminescence layer 12and hole-transporting layer 13, thereby increasing the luminescenceefficiency.

[0009] Further, in the structure of FIG. 1(b), an electron-transportinglayer 16 is disposed between the metal electrode 11 and the luminescencelayer 12. By separating the luminescence and the electron andhole-transportation to provide a more effective carrier blockingstructure, effective luminescence can be performed. For theelectron-transporting layer 16, an electron-transporting material, suchas an oxidiazole derivative, is used.

[0010] Known luminescence processes used heretofore in organic ELdevices include one utilizing an excited singlet state and one utilizingan excited triplet state, and the transition from the former state tothe ground state is called “fluorescence” and the transition from thelatter state to the ground state is called “phosphorescence”. And thesubstances in these excited states are called a singlet exciton and atriplet exciton, respectively.

[0011] In most of the organic luminescence devices studied heretofore,fluorescence caused by the transition from the excited singlet state tothe ground state, has been utilized. On the other hand, in recent years,devices utilizing phosphorescence via triplet excitons have beenstudied.

[0012] Representative published literature may include:

[0013] Article 1: Improved energy transfer in electrophosphorescentdevice (D. F. O'Brien, et al., Applied Physics Letters, Vol. 74, No. 3,p. 422 (1999)); and

[0014] Article 2: Very high-efficiency green organic light-emittingdevices based on electrophosphorescence (M. A. Baldo, et al., AppliedPhysics Letters, Vol. 75, No. 1, p. 4 (1999)).

[0015] In these articles, a structure including 4 organic layers devicesas shown in FIG. 1(c) has been principally used, including, from theanode side, a hole-transporting layer 13, a luminescence layer 12, anexciton diffusion-prevention layer 17 and an electron-transporting layer11. Materials used therein include carrier-transporting materials andphosphorescent materials, of which the names and structures are shownbelow together with their abbreviations.

[0016] Alq3: aluminum quinolinol complex

[0017] α-NPD:N4,N4′-di-naphthalene-1-yl-N4,N4′-diphenyl-biphenyl-4,4′-diamine

[0018] CBP: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline

[0019] PtOEP: platinum-octaethylporphyrin complex

[0020] Ir(ppy)₃: iridium-phenylpyrimidine complex

[0021] The above-mentioned Articles 1 and 2 both have reportedstructures, as exhibiting a high efficiency, including ahole-transporting layer 13 comprising α-NPD, an electron-transportinglayer 16 comprising Alq3, an exciton diffusion-preventing layer 17comprising BCP, and a luminescence layer 12 comprising CBP as a host andca. 6% of platinum-octaethylporphyrin complex (PtOEP) oriridium-phenylpyrimidine complex (Ir(ppy)₃) as a phosphorescent materialdispersed in mixture therein.

[0022] Such a phosphorescent material is particularly noted at presentbecause it is expected to provide a high luminescence efficiency inprinciple for the following reasons. More specifically, excitons formedby carrier recombination comprise singlet excitons and triplet excitonsin a probability ratio of 1:3. Conventional organic EL devices haveutilized fluorescence of which the luminescence efficiency is limited toat most 25%. On the other hand, if phosphorescence generated fromtriplet excitons is utilized, an efficiency of at least three times isexpected, and even an efficiency of 100%, i.e., four times, can beexpected in principle, if a transition owing to intersystem crossingfrom a singlet state having a higher energy to a triplet state is takeninto account.

[0023] However, like a fluorescent-type device, such an organicluminescence device utilizing phosphorescence is generally required tobe further improved regarding the deterioration of luminescenceefficiency and device stability.

[0024] The reason of the deterioration has not been fully clarified, butthe present inventors consider as follows based on the mechanism ofphosphorescence.

[0025] In the case where the luminescence layer comprises a hostmaterial having a carrier-transporting function and a phosphorescentguest material, a process of phosphorescence via triplet excitons mayinclude unit processes as follows:

[0026] 1. transportation of electrons and holes within a luminescencelayer,

[0027] 2. formation of host excitons,

[0028] 3. excitation energy transfer between host molecules,

[0029] 4. excitation energy transfer from the host to the guest,

[0030] 5. formation of guest triplet excitons, and

[0031] 6. transition of the guest triplet excitons to the ground stateand phosphorescence.

[0032] Desirable energy transfer in each unit process and luminescenceare caused in competition with various energy deactivation processes.

[0033] Particularly, in a phosphorescent material, this may beattributable to a life of the triplet excitons which is longer by threeor more digits than the life of a singlet exciton. More specifically,because it is held in a high-energy excited state for a longer period,it is liable to react with surrounding materials and cause polymerformation among the excitons, thus incurring a higher probability ofdeactivation process resulting in a material change or lifedeterioration, as we have considered.

[0034] Needless to say, a luminescence efficiency of an organicluminescence device is increased by increasing the luminescence quantumyield of a luminescence center material, but is is also an importantfactor for enhancing the luminescence intensity of the device toincrease the concentration of a luminescence material in theluminescence layer.

[0035] The luminescence intensity is increased in proportion to theconcentration of a luminescence material in a luminescence layer in thecase of a low concentration (up to several wt. %) of the luminescencematerial in the luminescence layer. However, above several % or 7%, adeviation from the proportional relationship is observed, and theluminescence intensity is rather lowered to result in a worseefficiency. This phenomenon is reported in Japanese Laid-Open PatentApplication (JP-A) 05-078655, JP-A 05-320633, etc., and is known asconcentration extinction or concentration deactivation.

[0036] Actually, in the case of using Ir(ppy)₃ in CBP as the hostmaterial, the best luminescence efficiency is attained at aconcentration of ca. 6 -7%, and the luminescence efficiency is ratherlowered thereabove, down to about a half at 12% concentration and 1/10or below at 100% concentration (Applied Physics Letters 4, vol. 75,1999).

[0037] The phenomenon is caused by abundant presence of molecules in thetriplet excited state waiting for luminescence in the case of aphosphorescence substance having a life of triplet exciton longer by 3digits or more than the life of singlet exciton. In this state, thermaldeactivation of losing energy due to mutual interaction of tripletexcitons is liable to occur. This is called triplet-triplet extinctionand is associated with a lowering in luminescence efficiency at a highcurrent density. Further, it is also considered that due to a longretention time at a high energy state, the excitons are caused to havean increased probability of reaction with a surrounding material andformation of polymers of excitons causing deactivation, or even leadingto material change or deterioration of life.

DISCLOSURE OF INVENTION

[0038] An object of the present invention is to provide an organicluminescence device of a higher luminescence intensity by suppressingthe above-mentioned concentration extinction phenomenon and providing anenvironment of using a luminescence material at a higher concentration.

[0039] More specifically, an object of the present invention is toprovide a luminescence material less liable to cause concentrationextinction even when used at a high concentration with respect to thehost material in a luminescence layer by introducing a substituent groupinto a metal coordination compound as such a luminescence material.

[0040] A more specific object of the present invention is to provide anorganic luminescence device capable of a large luminescence intensity,that is an organic luminescence device, comprising: a pair of electrodeseach disposed on a substrate, and at least one luminescence layercomprising an organic compound disposed between the electrodes; whereinthe luminescence layer comprises a non-luminescent first organiccompound and a phosphorescent second organic Compound represented byformula (1) shown below, and the second organic compound is present at aconcentration of at least 8 wt. % in the luminescence layer:

ML_(m)L′_(n)  (1),

[0041] wherein M is a metal atom of Ir, Pt, Rh or Pd; L and L′ aremutually different bidentate ligands; m is 1, 2 or 3; n is 0, 1 or 2with the proviso that m+n is 2 or 3; a partial structure ML_(m) isrepresented by formula (2) shown below and a partial structure ML′n isrepresented by formula (3), (4) or (5) shown below:

[0042] wherein N and C are nitrogen and carbon atoms, respectively; Aand A′ are respectively a cyclic group capable of having a substituentand bonded to the metal atom M via the carbon atom; B, B′ and B″ arerespectively a cyclic group represented by a formula of (6)-(14) shownbelow capable of having a substituent and connected to the metal atom Mvia the nitrogen atom:

[0043] According to another aspect, the organic luminescence device ofthe present invention is a luminescence device comprising one or plurallayers of organic film disposed between a cathode and an anode andincluding at least one layer of luminescence layer, that ischaracterized by containing a luminescence molecule of the formula (1)having a substituent and showing a maximum luminescence characteristicat a concentration higher than a concentration at which a luminescencemolecule of a similar structure but having no substituent shows amaximum luminescence efficiency.

[0044] More specifically, in a luminescence device comprising one orplural layers of organic film between a cathode and an anode, includingat least one layer of luminescence layer, it is preferred that aluminescence molecule of the formula (1) including at least one cyclicgroup having a substituent is contained at a concentration higher than aconcentration at which a luminescence molecule of a similar structureshows a maximum luminescence efficiency.

BRIEF DESCRIPTION OF THE DRAWINGS

[0045]FIG. 1 illustrates embodiments of the luminescence deviceaccording to the present invention.

[0046]FIG. 2 illustrates a simple matrix-type organic EL deviceaccording to Example 28.

[0047]FIG. 3 illustrates drive signals used in Example 28.

[0048]FIG. 4 schematically illustrates a panel structure including an ELdevice and drive means.

[0049]FIG. 5 illustrates an example of pixel circuit.

[0050]FIG. 6 is a schematic view showing an example of sectionalstructure of a TFT substrate.

BEST MODE FOR PRACTICING THE INVENTION

[0051] Basic device structures according to the present invention aresimilar to those shown in FIG. 1(a), (b) and (c).

[0052] More specifically, as shown in FIG. 1, an organic luminescencedevice generally comprises, on a transparent electrode 15, a 50 to 200nm-thick transparent electrode 14, a plurality of organic film layersand a 10 to 500 nm-thick metal electrode 11 formed so as to sandwich theorganic layers.

[0053]FIG. 1(a) shows an embodiment wherein the organic luminescencedevice comprises a luminescence layer 12 and a hole-transporting layer13. The transparent electrode 14 may comprise ITO, etc., having a largework function so as to facilitate hole injection from the transparentelectrode 14 to the hole-transporting layer 13. The metal electrode 11comprises a metal material having a small work function, such asaluminum, magnesium or alloys of these elements, so as to facilitateelectron injection into the organic luminescence device.

[0054] The luminescence layer 12 comprises a compound according to thepresent invention. The hole-transporting layer 13 may comprise, e.g., atriphenyldiamine derivative, as represented by α-NPD mentioned above,and also a material having an electron-donative property as desired.

[0055] A device organized above exhibits a current-rectifyingcharacteristic, and when an electric field is applied between the metalelectrode 11 as a cathode and the transparent electrode 14 as an anode,electrons are injected from the metal electrode 11 into the luminescencelayer 12, and holes are injected from the transparent electrode 15. Theinjected holes and electrons are recombined in the luminescence layer 12to form excitons, which cause luminescence. In this instance, thehole-transporting layer 13 functions as an electron-blocking layer toincrease the recombination efficiency at the boundary between theluminescence layer layer 12 and the hole-transporting layer 13, therebyproviding an enhanced luminescence efficiency.

[0056] Further, in the structure of FIG. 1(b), an electron-transportinglayer 16 is disposed between the metal electrode 11 and the luminescencelayer 12 in FIG. 1(a). As a result, the luminescence function isseparated from the functions of election transportation and holetransportation to provide a structure exhibiting more effective carrierblocking, thus increasing the luminescence efficiency. Theelectron-transporting layer 16, may comprise, e.g., an oxadiazolederivative.

[0057]FIG. 1(c) shows another desirable form of a four-layer structure,including a hole-transporting layer 13, a luminescence layer 12, anexciton diffusion prevention layer 17 and an electron-transporting layer16, successively from the side of the transparent electrode 14 as ananode.

[0058] Each of the organic film layers 12, 13, 16 and 17 is formed in athickness of at most 200 nm, and particularly the luminescence layer 12is formed in a thickness of 5 -200 nm.

[0059] The present inventors have got a knowledge that the use of ametal coordination compound including a substituted cyclic group andrepresented by the above-mentioned formula (1) allows a high efficiencyluminescence and provides less liability of concentration extinctioneven at a high concentration than the conventional level due tosuppression of inter-molecular interaction.

[0060] It has been also found that the suppression of concentrationextinction is an effect attributable to a substituent possessed by themetal coordination compound, and the concentration extinction becomesless liable to occur not regardless of the coordination number ofligands but owing to the presence of a substituent on at least oneligand.

[0061] Particularly, as a result, in a conventional phosphorescence-typeorganic EL device, the luminescence material can be used at a highconcentration of 8% or higher in the luminescence layer, therebyproviding an organic EL device exhibiting a high luminescence luminance.

[0062] The metal coordination compound used in the present inventionemits phosphorescence, and its lowest excited state is believed to be anMLCT* (metal-to-ligand charge transfer) excited state or π-π* excitedstate in a triplet state, and phosphorescence is caused at the time oftransition from such a state to the ground state.

[0063] It is generally said that phosphorescence life is shorter atMCLT* than at π-π*, but the molecular structure suppressing theconcentration extinction used in the present invention is effective forboth MCLT* and π-π* as the lowest excited state, and the molecule can bedoped at a high concentration in the luminescence layer in either case.

[0064] The luminescence material of the present invention exhibited ahigh phosphorescence yield of from 0.1 to 0.9 and a shortphosphorescence life of 0.1 -30 μsec. The phosphorescence yield referredto herein is a relative quantum yield, i.e., a ratio of an objectivesample's quantum yield φ(sample) to a standard sample's quantum yieldφ(st)) and is determined according to the following formula:

φ(sample)/φ(st)=[Sem(sample)/Iabs(sample)]/[Sem(st)/Iabs(st)],

[0065] wherein Iabs(st) denotes an absorption coefficient at anexcitation wavelength of the standard sample; Sem(st), a luminescencespectral areal intensity when excited at the same wavelength:Iabs(sample), an absorption coefficient at an excitation wavelength ofan objective compound; and Sem(sample), a luminescence spectral arealintensity when excited at the same wavelength.

[0066] Phosphorescence yield values described herein are relative valueswith respect to a phosphorescence yield φ=1 of Ir(ppy)₃ as a standardsample.

[0067] Further, the luminescence (phosphorescence) life referred toherein is based on values measured according to the following method.

[0068] <<Method of measurement of life>>

[0069] A sample compound is dissolved in chloroform and spin-coated ontoa quartz substrate in a thickness of ca. 0.1 μm and is exposed topulsative nitrogen laser light at an excitation wavelength of 337 nm atroom temperature by using a luminescence life meter (made by HamamatsuPhotonics K.K.). After completion of the excitation pulses, the decaycharacteristic of luminescence intensity is measured.

[0070] When an initial luminescence intensity is denoted by I₀, aluminescence intensity after t(sec) is expressed according to thefollowing formula with reference to a luminescence life τ(sec):

I=I₀·exp(−t/τ).

[0071] Thus, the luminescence life τ is a time period in which theluminescence intensity I is attenuated down to 1/e of the initialintensity I (I/I₀=e⁻¹, e is a base of natural logarithm).

[0072] A short phosphorescence life is a condition for providing an ELdevice of a high luminescence efficiency. More specifically, a longphosphorescence life means abundant presence of molecules in a tripletexcited state waiting for the luminescence leading to a problem of alowering in luminescence efficiency particularly at a high currentdensity. The material of the present invention is a suitableluminescence material for an EL device because of a high phosphorescenceyield and a short phosphorescence life. Further, it is assumed thatbecause of a short phosphorescence life, the duration at a triplet stateis shortened to suppress the concentration extinction. A high stabilityof the luminescence material of the present invention was also exhibitedin an actual current conduction test of actual devices.

[0073] In the case of a phosphorescent material, the luminescencecharacteristic thereof is severely affected by its molecularenvironment. In the case of a fluorescence device, the basic property ofa luminescence material is examined based on photoluminescence. In thecase of phosphorescence, however, the photoluminescence performance doesnot directly lead to the luminescence performance of an EL device sinceit is frequently affected by the polarity of host molecules, temperatureand solid/liquid state. As a result, EL device performances except for apart thereof cannot be estimated from the photoluminescence result.

[0074] In the case of a ligand of the present invention having a cyclicgroup having one or plural fluorine atoms, it becomes possible to shiftthe luminescence wavelength to a shorter side or a longer side becauseof a change in energy gap. If it is assumed for convenience thatHOMO/LUMO of metal electron orbits and HOMO/LUMO of ligand electronorbits can be considered separately, it is understood that MOHO/LUMOenergy levels of ligand electron orbits are changed by fluorine atomshaving a large electro-negativity to change the energy gap between theHOMO level of the metal and the LUMO level of the ligand, therebyshifting the luminescence from the MCLT state as the lowest excitedstate to a shorter wavelength side or a longer wavelength side.Accordingly, while a luminescence material exhibiting a stably highquantum yield over a broad wavelength range (blue to red) has not beenfound, it can be realized by a luminescence material of the presentinvention, thus being able to provide a luminescence material whichshows a high efficiency at a desired emission wavelength over a boardwavelength range (from blue to red).

[0075] When a device is formed, due to a large electronegativity offluorine atoms, the inter-molecular interaction is suppressed tophysically result in a suppressed crystallinity favoring a uniform filmformation and physically suppressing the dimerization reaction toprohibit the energy deactivation leading to an improved luminescenceefficiency, thus resulting in an improved electrical property and animproved device stability.

[0076] Further, in the case of using a ligand containing a plurality offluorine atoms or polyfluoroalkyl groups as substituents, it isconsidered that direct interaction between luminescence molecules issuppressed due to electrical repulsion caused by their electrical effector due to steric hindrance, thereby preventing energy deactivation andconcentration extinction.

[0077] Further, from the viewpoint of device preparation, a luminescencematerial having a substituent, particularly a fluorinated substituent,allows easier vacuum deposition due to a lowering in sublimationtemperature in the film formation by vacuum deposition, thus providing agreat advantage also in this respect.

[0078] As a result, as shown in Examples described hereinafter, by usinga luminescence material having a substituent according to the presentinvention, a stable luminescence for long hours with suppressedconcentration extinction can be expected. Further, it becomes possibleto attain a high phosphorescence yield over a temperature range of from−20° C. to 60° C. as an actual operation temperature range of an organicluminescence device. Further, in the case of using a compound at aconcentration of 8 wt. % or higher with respect to a host material inthe luminescence layer or at a concentration higher than a compoundhaving no substituent, it becomes possible to provide an EL deviceexhibiting excellent luminescence performance while suppressing theconcentration extinction. The concentration of the luminescence materialof the present invention in the luminescence layer may be at least 8 wt.%, preferably 10 wt. % or higher, but the luminescence materialpotentially has a possibility of being used even at 100% without causingsubstantial concentration extinction.

[0079] Herein, the term “luminescence performance” refers to acharacteristic attributable to a maximum luminescence efficiency whichcan be expressed as any of a maximum luminance, a maximum ofluminance/current, a maximum of light flux/power consumption or amaximum of external quantum yield.

[0080] A high-efficiency luminescence device according to the presentinvention is applicable to a product requiring energy economization or ahigh luminance. More specifically, the luminescence device is applicableto a display apparatus, an illumination apparatus, a printer lightsource or a backlight for a luminescence layer display apparatus. As fora display apparatus, it allows a flat panel display which is light inweight and provides a highly recognizable display at a low energyconsumption. As a printer light source, the luminescence device of thepresent invention can be used instead of a laser light source of a laserbeam printer. Independently addressable devices are arranged in an arrayform to effect a desired exposure on a photosensitive drum therebyforming an image. The apparatus volume can be remarkably reduced byusing the devices of the present invention. For the illuminationapparatus or backlight, the energy economization effect according to thepresent invention can be expected.

[0081] For the application to a display, a drive system using athin-film transistor (abbreviated as TFT) drive circuit according to anactive matrix-scheme, may be used. By driving a display panel using aluminescence material of the present invention in a luminescence layer,it becomes possible to allow a stable display for long hours at a goodpicture quality.

[0082] Hereinbelow, some specific structural formulae of metalcoordination compounds represented by the formula (1) used in thepresent invention are shown in Table 1 appearing hereinafter, which arehowever only representative examples and are not exhaustive. Ph-P9 usedin Table 1 represent partial structures shown below, of whichsubstituents R1, R2, . . . ate shown as A-R1, A-R2, . . . when containedin the cyclic group A in the formula (1) and as B-R1, B-R2, . . . whencontained in the cyclic qroup B, . . . in Table 1.

TABLE 1-1 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8  1 Ir 3 0Ph P1 CH3 H H H H H H H  2 Ir 3 0 Ph P1 H CH3 H H H H H H  3 Ir 3 0 PhP1 H H CH3 H H H H H  4 Ir 3 0 Ph P1 H H H CH3 H H H H  5 Ir 3 0 Ph P1C2H5 H H H H H H H  6 Ir 3 0 Ph P1 H C2H5 H H H H H H  7 Ir 3 0 Ph P1 HH C2H5 H H H H H  8 Ir 3 0 Ph P1 H H H C2H5 H H H H  9 Ir 3 0 Ph P1 C3H7H H H H H H H 10 Ir 3 0 Ph P1 H C3H7 H H H H H H 11 Ir 3 0 Ph P1 H HC3H7 H H H H H 12 Ir 3 0 Ph P1 H H H C3H7 H H H H 13 Ir 3 0 Ph P1 C4H9 HH H H H H H 14 Ir 3 0 Ph P1 H C4H9 H H H H H H 15 Ir 3 0 Ph P1 H H C4H9H H H H H 16 Ir 3 0 Ph P1 H H H C4H9 H H H H 17 Ir 3 0 Ph P1 C6H13 H H HH H H H 18 Ir 3 0 Ph P1 — C6H13 H H H H H H 19 Ir 3 0 Ph P1 H H C6H13 HH H H H 20 Ir 3 0 Ph P1 H H H C6H13 H H H H 21 Ir 3 0 Ph P1 C8H17 H H HH H H H 22 Ir 3 0 Ph P1 H C8H17 H H H H H H 23 Ir 3 0 Ph P1 H H C8H17 HH H H H 24 Ir 3 0 Ph P1 H H H C8H17 H H H H 25 Ir 3 0 Ph P1 C12H25 H H HH H H H 26 Ir 3 0 Ph P1 H C12H25 H H H H H H 27 Ir 3 0 Ph P1 H H C12H25H H H H H 28 Ir 3 0 Ph P1 H H H C12H25 H H H H 29 Ir 3 0 Ph P1 C15H31 HH H H H H H 30 Ir 3 0 Ph P1 H C15H31 H H H H H H 31 Ir 3 0 Ph P1 H HC15H31 H H H H H 32 Ir 3 0 Ph P1 H H CH3O H H H H H 33 Ir 3 0 Ph P1 H HC2H5O H H H H H 34 Ir 3 0 Ph P1 H H C4H9O H H H H H 35 Ir 3 0 Ph P1 HC4H9O H H H H H H 36 Ir 3 0 Ph P1 H

H H H H H H 37 Ir 3 0 Ph P1 H

H H H H H H 38 Ir 3 0 Ph P1 H H

H H H H H 39 Ir 3 0 Ph P1 H H

H H H H H 40 Ir 3 0 Ph P1 H H CF3O H H H H H 41 Ir 3 0 Ph P1 H H C4F9 HH H H H 42 Ir 3 0 Ph P1 H C4F9 H H H H H H 43 Ir 3 0 Ph P1 H H C2F5CH2OH H H H H 44 Ir 3 0 Ph P1 H C2F5 H H H H H H 45 Ir 3 0 Ph P1 H H C2F5 HH H H H 46 Ir 3 0 Ph P1 H H C5F11 H H H H H 47 Ir 3 0 Ph P1 H H C8F17 HH H H H 48 Ir 3 0 Ph P1 H H C2F5C2H4 H H H H H 49 Ir 3 0 Ph P1 CH3 H CH3H H H H H 50 Ir 3 0 Ph P1 H CH3 CH3 H H H H H 51 Ir 3 0 Ph P1 C2H5 HC2H5 H H H H H 52 Ir 3 0 Ph P1 C4H9 H C4H9 H H H H H 53 Ir 3 0 Ph P1 HC4H9 H H H H H H 54 Ir 3 0 Ph P1 H H H H CH3 H H H 55 Ir 3 0 Ph P1 H H HH H CH3 H H 56 Ir 3 0 Ph P1 H H H H H H CH3 H 57 Ir 3 0 Ph P1 H H H H HH H CH3 58 Ir 3 0 Ph P1 H H H H C4H9 H H H 59 Ir 3 0 Ph P1 H H H H HC4H9 H H 60 Ir 3 0 Ph P1 H H H H H H C4H9 H

[0083] TABLE 1-2 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8 61Ir 3 0 Ph P1 H H H H H H H C4H9 62 Ir 3 0 Ph P1 H H H H C8H17 H H H 63Ir 3 0 Ph P1 H H H H H C8H17 H H 64 Ir 3 0 Ph P1 H H H H H H C8H17 H 65Ir 3 0 Ph P1 H H H H H H H C8H17 66 Ir 3 0 Ph P1 CH3 H H H CH3 H H H 67Ir 3 0 Ph P1 CH3 H H H H CH3 H H 68 Ir 3 0 Ph P1 CH3 H H H H H CH3 H 69Ir 3 0 Ph P1 CH3 H H H H H H CH3 70 Ir 3 0 Ph P1 H CH3 H H CH3 H H H 71Ir 3 0 Ph P1 H CH3 H H H CH3 H H 72 Ir 3 0 Ph P1 H CH3 H H H H CH3 H 73Ir 3 0 Ph P1 H CH3 H H H H H CH3 74 Ir 3 0 Ph P1 H H CH3 H CH3 H H H 75Ir 3 0 Ph P1 H H CH3 H H CH3 H H 76 Ir 3 0 Ph P1 H H CH3 H H H CH3 H 77Ir 3 0 Ph P1 H H CH3 H H H H CH3 78 Ir 3 0 Ph P1 H H H CH3 H H CH3 H 79Ir 3 0 Ph P1 C2H5 H H H H CH3 H H 80 Ir 3 0 Ph P1 C2H5 H H H H H CH3 H81 Ir 3 0 Ph P1 H C2H5 H H CH3 H H H 82 Ir 3 0 Ph P1 H C2H5 H H H CH3 HH 83 Ir 3 0 Ph P1 H C2H5 H H H H CH3 H 84 Ir 3 0 Ph P1 H C2H5 H H H H HCH3 85 Ir 3 0 Ph P1 H H C2H5 H CH3 H H H 86 Ir 3 0 Ph P1 H H C2H5 H HCH3 H H 87 Ir 3 0 Ph P1 H H C2H5 H H H CH3 H 88 Ir 3 0 Ph P1 H H C2H5 HH H H CH3 89 Ir 3 0 Ph P1 H H H C2H5 H CH3 H H 90 Ir 3 0 Ph P1 H H HC2H5 H H CH3 H 91 Ir 3 0 Ph P1 C4H9 H H H H CH3 H H 92 Ir 3 0 Ph P1 HC4H9 H H CH3 H H H 93 Ir 3 0 Ph P1 H C4H9 H H H CH3 H H 94 Ir 3 0 Ph P1H C4H9 H H H H CH3 H 95 Ir 3 0 Ph P1 H C4H9 H H H H H CH3 96 Ir 3 0 PhP1 H H C4H9 H H CH3 H H 97 Ir 3 0 Ph P1 H H C4H9 H H H CH3 H 98 Ir 3 0Ph P1 H H H C4H9 H CH3 H H 99 Ir 3 0 Ph P1 H H H C4H9 H CH3 H H 100 Ir 30 Ph P1 C6H13 H H H H CH3 H H 101 Ir 3 0 Ph P1 H C6H13 H H CH3 H H H 102Ir 3 0 Ph P1 H C6H13 H H H CH3 H H 103 Ir 3 0 Ph P1 H C6H13 H H H H CH3H 104 Ir 3 0 Ph P1 H C6H13 H H H H H CH3 105 Ir 3 0 Ph P1 H H C6H13 H HCH3 H H 106 Ir 3 0 Ph P1 H H C6H13 H H H CH3 H 107 Ir 3 0 Ph P1 H H HC6H13 H CH3 H H 108 Ir 3 0 Ph P1 H H H C6H13 H CH3 H H 109 Ir 3 0 Ph P1CH3 H H H CF3 H H H 110 Ir 3 0 Ph P1 H CH3 H H CF3 H H H 111 Ir 3 0 PhP1 H H CH3 H CF3 H H H 112 Ir 3 0 Ph P1 H H H CH3 CF3 H H H 113 Ir 3 0Ph P1 CH3 H H H H CF3 H H 114 Ir 3 0 Ph P1 H CH3 H H H CF3 H H 115 Ir 30 Ph P1 H H CH3 H H CF3 H H 116 Ir 3 0 Ph P1 H H H CH3 H CF3 H H 117 Ir3 0 Ph P1 CH3 H H H H H CF3 H 118 Ir 3 0 Ph P1 H CH3 H H H H CF3 H 119Ir 3 0 Ph P1 H H CH3 H H H CF3 H 120 Ir 3 0 Ph P1 H H H CH3 H H CF3 H

[0084] TABLE 1-3 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8121 Ir 3 0 Ph P1 CH3 H H H H H H CF3 122 Ir 3 0 Ph P1 H CH3 H H H H HCF3 123 Ir 3 0 Ph P1 H H CH3 H H H H CF3 124 Ir 3 0 Ph P1 H H H CH3 H HH CF3 125 Ir 3 0 Ph P1 CH3 H H H F H H H 126 Ir 3 0 Ph P1 H CH3 H H F HH H 127 Ir 3 0 Ph P1 H H CH3 H F H H H 128 Ir 3 0 Ph P1 H H H CH3 F H HH 129 Ir 3 0 Ph P1 CH3 H H H H F H H 130 Ir 3 0 Ph P1 H CH3 H H H F H H131 Ir 3 0 Ph P1 H H CH3 H H F H H 132 Ir 3 0 Ph P1 H H H CH3 H F H H133 Ir 3 0 Ph P1 CH3 H H H H H F H 134 Ir 3 0 Ph P1 H CH3 H H H H F H135 Ir 3 0 Ph P1 H H CH3 H H H F H 136 Ir 3 0 Ph P1 H H H CH3 H H F H137 Ir 3 0 Ph P1 CH3 H H H H H H F 138 Ir 3 0 Ph P1 H CH3 H H H H H F139 Ir 3 0 Ph P1 H H CH3 H H H H F 140 Ir 3 0 Ph P1 H H H CH3 H H H F141 Ir 3 0 Ph P1 C2H5 H H H CF3 H H H 142 Ir 3 0 Ph P1 H C2H5 H H CF3 HH H 143 Ir 3 0 Ph P1 H H C2H5 H CF3 H H H 144 Ir 3 0 Ph P1 H H H C2H5CF3 H H H 145 Ir 3 0 Ph P1 C2H5 H H H H CF3 H H 146 Ir 3 0 Ph P1 H C2H5H H H CF3 H H 147 Ir 3 0 Ph P1 H H C2H5 H H CF3 H H 148 Ir 3 0 Ph P1 H HH C2H5 H CF3 H H 149 Ir 3 0 Ph P1 C2H5 H H H H H CF3 H 150 Ir 3 0 Ph P1H C2H5 H H H H CF3 H 151 Ir 3 0 Ph P1 H H C2H5 H H H CF3 H 152 Ir 3 0 PhP1 H H H C2H5 H H CF3 H 153 Ir 3 0 Ph P1 C2H5 H H H H H H CF3 154 Ir 3 0Ph P1 H C2H5 H H H H H CF3 155 Ir 3 0 Ph P1 H H C2H5 H H H H CF3 156 Ir3 0 Ph P1 H H H C2H5 H H H CF3 157 Ir 3 0 Ph P1 C2H5 H H H F H H H 158Ir 3 0 Ph P1 H C2H5 H H F H H H 159 Ir 3 0 Ph P1 H H C2H5 H F H H H 160Ir 3 0 Ph P1 H H H C2H5 F H H H 161 Ir 3 0 Ph P1 C2H5 H H H H F H H 162Ir 3 0 Ph P1 H C2H5 H H H F H H 163 Ir 3 0 Ph P1 H H C2H5 H H F H H 164Ir 3 0 Ph P1 H H H C2H5 H F H H 165 Ir 3 0 Ph P1 C2H5 H H H H H F H 166Ir 3 0 Ph P1 H C2H5 H H H H F H 167 Ir 3 0 Ph P1 H H C2H5 H H H F H 168Ir 3 0 Ph P1 H H H C2H5 H H F H 169 Ir 3 0 Ph P1 C2H5 H H H H H H F 170Ir 3 0 Ph P1 H C2H5 H H H H H F 171 Ir 3 0 Ph P1 H H C2H5 H H H H F 172Ir 3 0 Ph P1 H H H C2H5 H H H F 173 Ir 3 0 Ph P1 C4H9 H H H F H H H 174Ir 3 0 Ph P1 H C4H9 H H F H H H 175 Ir 3 0 Ph P1 H H C4H9 H F H H H 176Ir 3 0 Ph P1 H H H C4H9 F H H H 177 Ir 3 0 Ph P1 C4H9 H H H H F H H 178Ir 3 0 Ph P1 H C4H9 H H H F H H 179 Ir 3 0 Ph P1 H H C4H9 H H F H H 180Ir 3 0 Ph P1 H H H C4H9 H F H H

[0085] TABLE 1-4 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8181 Ir 3 0 Ph P1 C4H9 H H H H H F H 182 Ir 3 0 Ph P1 H C4H9 H H H H F H183 Ir 3 0 Ph P1 H H C4H9 H H H F H 184 Ir 3 0 Ph P1 H H H C4H9 H H F H185 Ir 3 0 Ph P1 C4H9 H H H H H H F 186 Ir 3 0 Ph P1 H C4H9 H H H H H F187 Ir 3 0 Ph P1 H H C4H9 H H H H F 188 Ir 3 0 Ph P1 H H H C4H9 H H H F189 Ir 3 0 Ph P1 C4H9 H H H CF3 H H H 190 Ir 3 0 Ph P1 H C4H9 H H CF3 HH H 191 Ir 3 0 Ph P1 H H C4H9 H CF3 H H H 192 Ir 3 0 Ph P1 H H H C4H9CF3 H H H 193 Ir 3 0 Ph P1 C4H9 H H H H CF3 H H 194 Ir 3 0 Ph P1 H C4H9H H H CF3 H H 195 Ir 3 0 Ph P1 H H C4H9 H H CF3 H H 196 Ir 3 0 Ph P1 H HH C4H9 H CF3 H H 197 Ir 3 0 Ph P1 C4H9 H H H H H CF3 H 198 Ir 3 0 Ph P1H C4H9 H H H H CF3 H 199 Ir 3 0 Ph P1 H H C4H9 H H H CF3 H 200 Ir 3 0 PhP1 H H H C4H9 H H CF3 H 201 Ir 3 0 Ph P1 C4H9 H H H H H H CF3 202 Ir 3 0Ph P1 H C4H9 H H H H H CF3 203 Ir 3 0 Ph P1 H H C4H9 H H H H CF3 204 Ir3 0 Ph P1 H H H C4H9 H H H CF3 205 Ir 3 0 Ph P1 C8H17 H H H F H H H 206Ir 3 0 Ph P1 H C8H17 H H F H H H 207 Ir 3 0 Ph P1 H H C8H17 H F H H H208 Ir 3 0 Ph P1 H H H C8H17 F H H H 209 Ir 3 0 Ph P1 C8H17 H H H H F HH 210 Ir 3 0 Ph P1 H C8H17 H H H F H H 211 Ir 3 0 Ph P1 H H C8H17 H H FH H 212 Ir 3 0 Ph P1 H H H C8H17 H F H H 213 Ir 3 0 Ph P1 C8H17 H H H HH F H 214 Ir 3 0 Ph P1 H C8H17 H H H H F H 215 Ir 3 0 Ph P1 H H C8H17 HH H F H 216 Ir 3 0 Ph P1 H H H C8H17 H H F H 217 Ir 3 0 Ph P1 C8H17 H HH H H H F 218 Ir 3 0 Ph P1 H C8H17 H H H H H F 219 Ir 3 0 Ph P1 H HC8H17 H H H H F 220 Ir 3 0 Ph P1 H H H C8H17 H H H F 221 Ir 3 0 Ph P1C8H17 H H H CF3 H H H 222 Ir 3 0 Ph P1 H C8H17 H H CF3 H H H 223 Ir 3 0Ph P1 H H C8H17 H CF3 H H H 224 Ir 3 0 Ph P1 H H H C8H17 CF3 H H H 225Ir 3 0 Ph P1 C8H17 H H H H CF3 H H 226 Ir 3 0 Ph P1 H C8H17 H H H CF3 HH 227 Ir 3 0 Ph P1 H H C8H17 H H CF3 H H 228 Ir 3 0 Ph P1 H H H C8H17 HCF3 H H 229 Ir 3 0 Ph P1 C8H17 H H H H H CF3 H 230 Ir 3 0 Ph P1 H C8H17H H H H CF3 H 231 Ir 3 0 Ph P1 H H C8H17 H H H CF3 H 232 Ir 3 0 Ph P1 HH H C8H17 H H CF3 H 233 Ir 3 0 Ph P1 C8H17 H H H H H H CF3 234 Ir 3 0 PhP1 H C8H17 H H H H H CF3 235 Ir 3 0 Ph P1 H H C8H17 H H H H CF3 236 Ir 30 Ph P1 H H H C8H17 H H H CF3 237 Ir 3 0 Ph P1 F H H H H H H H 238 Ir 30 Ph P1 H F H H H H H H 239 Ir 3 0 Ph P1 H H F H H H H H 240 Ir 3 0 PhP1 H H H F H H H H

[0086] TABLE 1-5 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8241 Ir 3 0 Ph P1 F F H H H H H H 242 Ir 3 0 Ph P1 F H F H H H H H 243 Ir3 0 Ph P1 H F H F H H H H 244 Ir 3 0 Ph P1 H F F H H H H H 245 Ir 3 0 PhP1 H F H H H H H H 246 Ir 3 0 Ph P1 H H H F H H H H 247 Ir 3 0 Ph P1 H HF F H H H H 248 Ir 3 0 Ph P1 F H F F H H H H 249 Ir 3 0 Ph P1 F F F H HH H H 250 Ir 3 0 Ph P1 H F F F H H H H 251 Ir 3 0 Ph P1 F F F H H H H H252 Ir 3 0 Ph P1 F F F F H H H H 253 Ir 3 0 Ph P1 F H H H CH3 H H H 254Ir 3 0 Ph P1 F H H H H CH3 H H 255 Ir 3 0 Ph P1 F H H H H H CH3 H 256 Ir3 0 Ph P1 F H H H H H H CH3 257 Ir 3 0 Ph P1 H F H H CH3 H H H 258 Ir 30 Ph P1 H F H H H CH3 H H 259 Ir 3 0 Ph P1 H F H H H H CH3 H 260 Ir 3 0Ph P1 H F H H H H H CH3 261 Ir 3 0 Ph P1 H H F H CH3 H H H 262 Ir 3 0 PhP1 H H F H H CH3 H H 263 Ir 3 0 Ph P1 H H F H H H CH3 H 264 Ir 3 0 Ph P1H H F H H H H CH3 265 Ir 3 0 Ph P1 H H H F CH3 H H H 266 Ir 3 0 Ph P1 HH H F H CH3 H H 267 Ir 3 0 Ph P1 H H H F H H CH3 H 268 Ir 3 0 Ph P1 H HH F H H H CH3 269 Ir 3 0 Ph P1 F F H H CH3 H H H 270 Ir 3 0 Ph P1 F F HH H CH3 H H 271 Ir 3 0 Ph P1 F F H H H H CH3 H 272 Ir 3 0 Ph P1 F F H HH H H CH3 273 Ir 3 0 Ph P1 F H F H CH3 H H H 274 Ir 3 0 Ph P1 F H F H HCH3 H H 275 Ir 3 0 Ph P1 F H F H H H CH3 H 276 Ir 3 0 Ph P1 F H F H H HH CH3 277 Ir 3 0 Ph P1 F H H F CH3 H H H 278 Ir 3 0 Ph P1 F H H F H CH3H H 279 Ir 3 0 Ph P1 F H H F H H CH3 H 280 Ir 3 0 Ph P1 F H H F H H HCH3 281 Ir 3 0 Ph P1 H F F H CH3 H H H 282 Ir 3 0 Ph P1 H F F H H CH3 HH 283 Ir 3 0 Ph P1 H F F H H H CH3 H 284 Ir 3 0 Ph P1 H F F H H H H CH3285 Ir 3 0 Ph P1 H F H F CH3 H H H 286 Ir 3 0 Ph P1 H F H F H CH3 H H287 Ir 3 0 Ph P1 H F H F H H CH3 H 288 Ir 3 0 Ph P1 H F H F H H H CH3289 Ir 3 0 Ph P1 H H F F CH3 H H H 290 Ir 3 0 Ph P1 H H F F H CH3 H H291 Ir 3 0 Ph P1 H H F F H H CH3 H 292 Ir 3 0 Ph P1 H H F F H H H CH3293 Ir 3 0 Ph P1 F F F H CH3 H H H 294 Ir 3 0 Ph P1 F F F H H CH3 H H295 Ir 3 0 Ph P1 F F F H H H CH3 H 296 Ir 3 0 Ph P1 F F F H H H H CH3297 Ir 3 0 Ph P1 F F H F CH3 H H H 298 Ir 3 0 Ph P1 F F H F H CH3 H H299 Ir 3 0 Ph P1 F F H F H H CH3 H 300 Ir 3 0 Ph P1 F F H F H H H CH3

[0087] TABLE 1-6 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8301 Ir 3 0 Ph P1 F H F F CH3 H H H 302 Ir 3 0 Ph P1 F H F F H CH3 H H303 Ir 3 0 Ph P1 F H F F H H CH3 H 304 Ir 3 0 Ph P1 F H F F H H H CH3305 Ir 3 0 Ph P1 F F F F CH3 H H H 306 Ir 3 0 Ph P1 F F F F H CH3 H H307 Ir 3 0 Ph P1 F F F F H H CH3 H 308 Ir 3 0 Ph P1 F F F F H H H CH3309 Ir 3 0 Ph P1 CF3 H H H H H H H 310 Ir 3 0 Ph P1 H CF3 H H H H H H311 Ir 3 0 Ph P1 H H CF3 H H H H H 312 Ir 3 0 Ph P1 H CF3 H CF3 H H H H313 Ir 3 0 Ph P1 CF3 CF3 H H H H H H 314 Ir 3 0 Ph P1 CF3 H CF3 H H H HH 315 Ir 3 0 Ph P1 CF3 H H CF3 H H H H 316 Ir 3 0 Ph P1 H CF3 CF3 H H HH H 317 Ir 3 0 Ph P1 H H C3F7C2H4 H H H H H 318 Ir 3 0 Ph P1 H H C7F15 HH H H H 319 Ir 3 0 Ph P1 H H CF3 CF3 H H H H 320 Ir 3 0 Ph P1 CF3 H CF3CF3 H H H H 321 Ir 3 0 Ph P1 CF3 CF3 CF3 H H H H H 322 Ir 3 0 Ph P1 HCF3 CF3 CF3 H H H H 323 Ir 3 0 Ph P1 CF3 CF3 CF3 H H H H H 324 Ir 3 0 PhP1 CF3 CF3 CF3 CF3 H H H H 325 Ir 3 0 Ph P1 CF3 H H H CH3 H H H 326 Ir 30 Ph P1 CF3 H H H H CH3 H H 327 Ir 3 0 Ph P1 CF3 H H H H H CH3 H 328 Ir3 0 Ph P1 CF3 H H H H H H CH3 329 Ir 3 0 Ph P1 H CF3 H H CH3 H H H 330Ir 3 0 Ph P1 H CF3 H H H CH3 H H 331 Ir 3 0 Ph P1 H CF3 H H H H CH3 H332 Ir 3 0 Ph P1 H CF3 H H H H H CH3 333 Ir 3 0 Ph P1 H H CF3 H CH3 H HH 334 Ir 3 0 Ph P1 H H CF3 H H CH3 H H 335 Ir 3 0 Ph P1 H H CF3 H H HCH3 H 336 Ir 3 0 Ph P1 H H CF3 H H H H CH3 337 Ir 3 0 Ph P1 H H H CF3CH3 H H H 338 Ir 3 0 Ph P1 H H H CF3 H CH3 H H 339 Ir 3 0 Ph P1 H H HCF3 H H CH3 H 340 Ir 3 0 Ph P1 H H H CH3 H H H CH3 341 Ir 3 0 Ph P1 CF3CF3 H H CH3 H H H 342 Ir 3 0 Ph P1 CF3 CF3 H H H CH3 H H 343 Ir 3 0 PhP1 CF3 CF3 H H H H CH3 H 344 Ir 3 0 Ph P1 CF3 CF3 H H H H H CH3 345 Ir 30 Ph P1 CF3 H CF3 H CH3 H H H 346 Ir 3 0 Ph P1 CF3 H CF3 H H CH3 H H 347Ir 3 0 Ph P1 CF3 H CF3 H H H CH3 H 348 Ir 3 0 Ph P1 CF3 H CF3 H H H HCH3 349 Ir 3 0 Ph P1 CF3 H H CF3 CH3 H H H 350 Ir 3 0 Ph P1 CF3 H H CF3H CH3 H H 351 Ir 3 0 Ph P1 CF3 H H CF3 H H CH3 H 352 Ir 3 0 Ph P1 CF3 HH CF3 H H H CH3 353 Ir 3 0 Ph P1 H CF3 CF3 H CH3 H H H 354 Ir 3 0 Ph P1H CF3 CF3 H H CH3 H H 355 Ir 3 0 Ph P1 H CF3 CF3 H H H CH3 H 356 Ir 3 0Ph P1 H CF3 CF3 H H H H CH3 357 Ir 3 0 Ph P1 H CF3 H CF3 CH3 H H H 358Ir 3 0 Ph P1 H CF3 H CF3 H CH3 H H 359 Ir 3 0 Ph P1 H CF3 H CF3 H H CH3H 360 Ir 3 0 Ph P1 H CF3 H CF3 H H H CH3

[0088] TABLE 1-7 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8361 Ir 3 0 Ph P1 H H CF3 CF3 CH3 H H H 362 Ir 3 0 Ph P1 H H CF3 CF3 HCH3 H H 363 Ir 3 0 Ph P1 H H CF3 CF3 H H CH3 H 364 Ir 3 0 Ph P1 H H CF3CF3 H H H CH3 365 Ir 3 0 Ph P1 CF3 CF3 CF3 H CH3 H H H 366 Ir 3 0 Ph P1CF3 CF3 CF3 H H CH3 H H 367 Ir 3 0 Ph P1 CF3 CF3 CF3 H H H CH3 H 368 Ir3 0 Ph P1 CF3 CF3 CF3 H H H H CH3 369 Ir 3 0 Ph P1 CF3 CF3 H CF3 CH3 H HH 370 Ir 3 0 Ph P1 CF3 CF3 H CF3 H CH3 H H 371 Ir 3 0 Ph P1 CF3 CF3 HCF3 H H CH3 H 372 Ir 3 0 Ph P1 CF3 CF3 H CF3 H H H CH3 373 Ir 3 0 Ph P1CF3 H CF3 CF3 CH3 H H H 374 Ir 3 0 Ph P1 CF3 H CF3 CF3 H CH3 H H 375 Ir3 0 Ph P1 CF3 H CF3 CF3 H H CH3 H 376 Ir 3 0 Ph P1 CF3 H CF3 CF3 H H HCH3 377 Ir 3 0 Ph P1 CF3 CF3 CF3 CF3 CH3 H H H 378 Ir 3 0 Ph P1 CF3 CF3CF3 CF3 H CH3 H H 379 Ir 3 0 Ph P1 CF3 CF3 CF3 CF3 H H CH3 H 380 Ir 3 0Ph P1 CF3 CF3 CF3 CF3 H H H CH3 381 Ir 3 0 Ph P1 F CF3 H H H H H H 382Ir 3 0 Ph P1 F CF3 H CF3 H H H H 383 Ir 3 0 Ph P1 F H H CF3 H H H H 384Ir 3 0 Ph P1 H CF3 F H H H H H 385 Ir 3 0 Ph P1 H CF3 F CF3 H H H H 386Ir 3 0 Ph P1 H H F CF3 H H H H 387 Ir 3 0 Ph P1 F CF3 F H H H H H 388 Ir3 0 Ph P1 F H F CF3 H H H H 389 Ir 3 0 Ph P1 H CH3 F H H H H H 390 Ir 30 Ph P1 H CH3 CF3 H H H H H 391 Ir 3 0 Ph P1 F CF3 H CF3 H H H H 392 Ir3 0 Ph P1 CF3 H F H H H H H 393 Ir 3 0 Ph P1 H CF3 F H H CH3 H H 394 Ir3 0 Ph P1 H CF3 F CF3 H CH3 H H 395 Ir 3 0 Ph P1 H H F CF3 H CH3 H H 396Ir 3 0 Ph P1 F CF3 F H H CH3 H H 397 Ir 3 0 Ph P1 F H F CF3 H CH3 H H398 Ir 3 0 Ph P1 F CF3 F CF3 H CH3 H H 399 Ir 3 0 Ph P1 F CF3 H H H HCH3 H 400 Ir 3 0 Ph P1 F CF3 H CF3 H H CH3 H 401 Ir 3 0 Ph P1 F H H CF3H H CH3 H 402 Ir 3 0 Ph P1 H CF3 F H H H CH3 H 403 Ir 3 0 Ph P1 H CF3 FCF3 H H CH3 H 404 Ir 3 0 Ph P1 H H F CF3 H H CH3 H 405 Ir 3 0 Ph P1 FCF3 F H H H CH3 H 406 Ir 3 0 Ph P1 F H F CF3 H H CH3 H 407 Ir 3 0 Ph P1F CF3 F CF3 H H CH3 H 408 Ir 3 0 Ph P1 F H H H H CF3 H H 409 Ir 3 0 PhP1 H F H H H CF3 H H 410 Ir 3 0 Ph P1 H H F H H CF3 H H 411 Ir 3 0 Ph P1H H H F H CF3 H H 412 Ir 3 0 Ph P1 F H H H H H CF3 H 413 Ir 3 0 Ph P1 HF H H H H CF3 H 414 Ir 3 0 Ph P1 H H F H H H CF3 H 415 Ir 3 0 Ph P1 H HH F H H CF3 H 416 Ir 3 0 Ph P1 H F H F H CF3 H H 417 Ir 3 0 Ph P1 H F HF H CF3 H H 418 Ir 3 0 Ph P1 H F H F H CF3 H H 419 Ir 3 0 Ph P1 H F H FH CF3 H H 420 Ir 3 0 Ph P1 H F H F H H CF3 H

[0089] TABLE 1-8 No M m n A B E J G A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7B-R8 421 Ir 3 0 Ph P1 — — — H F H F H H CF3 H 422 Ir 3 0 Ph P1 — — — H FH F H H CF3 H 423 Ir 3 0 Ph P1 — — — H F H F H H CF3 H 424 Ir 3 0 Ph P1— — — CF3 H H H H CF3 H H 425 Ir 3 0 Ph P1 — — — H CF3 H H H CF3 H H 426Ir 3 0 Ph P1 — — — H H CF3 H H CF3 H H 427 Ir 3 0 Ph P1 — — — H H H CF3H CF3 H H 428 Ir 3 0 Ph P1 — — — CF3 H H H H H CF3 H 429 Ir 3 0 Ph P1 —— — H CF3 H H H H CF3 H 430 Ir 3 0 Ph P1 — — — H H CF3 H H H CF3 H 431Ir 3 0 Ph P1 — — — H H H CF3 H H CF3 H 432 Ir 3 0 Ph P1 — — — CF3 H CF3H H CF3 H H 433 Ir 3 0 Ph P1 — — — H F CF3 H H CF3 H H 434 Ir 3 0 Ph P1— — — CF3 H CF3 H H CF3 H H 435 Ir 3 0 Ph P1 — — — H H H CF3 H CF3 H H436 Ir 3 0 Ph P1 — — — CF3 H CF3 H H H CF3 H 437 Ir 3 0 Ph P1 — — — H FCF3 H H H CF3 H 438 Ir 3 0 Ph P1 — — — CF3 H CF3 H H H CF3 H 439 Ir 3 0Ph P1 — — — H H H CF3 H H CF3 H 440 Ir 2 1 Ph P1 CH3 H CH3 CH3 H H H H HH H 441 Ir 2 1 Ph P1 CH3 H CH3 H CH3 H H H H H H 442 Ir 2 1 Ph P1 CH3 HCH3 H H CH3 H H H H H 443 Ir 2 1 Ph P1 CH3 H CH3 H H H CH3 H H H H 444Ir 2 1 Ph P1 CH3 H CH3 C2H5 H H H H H H H 445 Ir 2 1 Ph P1 CH3 H CH3 HC2H5 H H H H H H 446 Ir 2 1 Ph P1 CH3 H CH3 H H C2H5 H H H H H 447 Ir 21 Ph P1 CH3 H CH3 H H H C2H5 H H H H 448 Ir 2 1 Ph P1 CH3 H CH3 C3H7 H HH H H H H 449 Ir 2 1 Ph P1 CH3 H CH3 H C3H7 H H H H H H 450 Ir 2 1 Ph P1CH3 H CH3 H H C3H7 H H H H H 451 Ir 2 1 Ph P1 CH3 H CH3 H H H C3H7 H H HH 452 Ir 2 1 Ph P1 CH3 H CH3 C4H9 H H H H H H H 453 Ir 2 1 Ph P1 CH3 HCH3 H C4H9 H H H H H H 454 Ir 2 1 Ph P1 CH3 H CH3 H H C4H9 H H H H H 455Ir 2 1 Ph P1 CH3 H CH3 H H H C4H9 H H H H 456 Ir 2 1 Ph P1 CH3 H CH3C6H13 H H H H H H H 457 Ir 2 1 Ph P1 CH3 H CH3 — C6H13 H H H H H H 458Ir 2 1 Ph P1 CH3 H CH3 H H C6H13 H H H H H 459 Ir 2 1 Ph P1 CH3 H CH3 HH H C6H13 H H H H 460 Ir 2 1 Ph P1 CH3 H CH3 C8H17 H H H H H H H 461 Ir2 1 Ph P1 CH3 H CH3 H C8H17 H H H H H H 462 Ir 2 1 Ph P1 CH3 H CH3 H HC8H17 H H H H H 463 Ir 2 1 Ph P1 CH3 H CH3 H H H C8H17 H H H H 464 Ir 21 Ph P1 CH3 H CH3 C12H25 H H H H H H H 465 Ir 2 1 Ph P1 CH3 H CH3 HC12H25 H H H H H H 466 Ir 2 1 Ph P1 CH3 H CH3 H H C12H25 H H H H H 467Ir 2 1 Ph P1 CH3 H CH3 H H H C12H25 H H H H 468 Ir 2 1 Ph P1 CH3 H CH3C15H31 H H H H H H H 469 Ir 2 1 Ph P1 CH3 H CH3 H C15H31 H H H H H H 470Ir 2 1 Ph P1 CH3 H CH3 H H C15H31 H H H H H 471 Ir 2 1 Ph P1 CH3 H CH3 HH C15H31 H H H H 472 Ir 2 1 Ph P1 CH3 CH3 CH3 H H H H H H H H 473 Ir 2 1Ph P1 CH3 F CH3 H H H H H H H H 474 Ir 2 1 Ph P1 CF3 CH3 CF3 H H H H H HH H 475 Ir 2 1 Ph P1 CF3 F CF3 H H H H H H H H 476 Ir 2 1 Ph P1 CH3 CF3CH3 H H H H H H H H 477 Ir 2 1 Ph P1 C4H9 F C4H9 H H H H H H H H 478 Ir2 1 Ph P1 CH3 C2H5 CH3 H H H H H H H H 479 Ir 2 1 Ph P1 CH3 C4H9 CH3 H HH H H H H H 480 Ir 2 1 Ph P1 CH3 CH3 CH3 H CH3 H H H H H H

[0090] TABLE 1-9 No M m n A B E J G A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7B-R8 481 Ir 2 1 Ph P1 CH3 F CH3 H CH3 H H H H H H 482 Ir 2 1 Ph P1 CF3CH3 CF3 H CH3 H H H H H H 483 Ir 2 1 Ph P1 CF3 F CF3 H CH3 H H H H H H484 Ir 2 1 Ph P1 CH3 CF3 CH3 H CH3 H H H H H H 485 Ir 2 1 Ph P1 C4H9 FC4H9 H CH3 H H H H H H 486 Ir 2 1 Ph P1 CH3 C2H5 CH3 H CH3 H H H H H H487 Ir 2 1 Ph P1 CH3 H CH3 H F H H H H H H 488 Ir 2 1 Ph P1 CH3 CH3 CH3H F H H H H H H 489 Ir 2 1 Ph P1 CH3 H CH3 H H F H H H H H 490 Ir 2 1 PhP1 CF3 CH3 CF3 H F H H H H H H 491 Ir 2 1 Ph P1 CF3 F CF3 H F H H H H HH 492 Ir 2 1 Ph P1 CH3 CF3 CH3 H F H H H H H H 493 Ir 2 1 Ph P1 C4H9 FC4H9 H F H H H H H H 494 Ir 2 1 Ph P1 CH3 C2H5 CH3 H F H H H H H H 495Ir 2 1 Ph P1 CH3 H CH3 H CF3 H H H H H H 496 Ir 2 1 Ph P1 CH3 CH3 CH3 HCF3 H H H H H H 497 Ir 2 1 Ph P1 CH3 F CH3 H CF3 H H H H H H 498 Ir 2 1Ph P1 CF3 CH3 CF3 H CF3 H H H H H H 499 Ir 2 1 Ph P1 CF3 F CF3 H CF3 H HH H H H 500 Ir 2 1 Ph P1 CH3 CF3 CH3 H CF3 H H H H H H 501 Ir 2 1 Ph P1C4H9 F C4H9 H CF3 H H H H H H 502 Ir 2 1 Ph P1 CH3 C2H5 CH3 H CF3 H H HH H H 503 Ir 2 1 Ph P1 CH3 H CH3 H H H H H CH3 H H 504 Ir 2 1 Ph P1 CH3CH3 CH3 H H H H H CH3 H H 505 Ir 2 1 Ph P1 CH3 F CH3 H H H H H CH3 H H506 Ir 2 1 Ph P1 CF3 CH3 CF3 H H H H H CH3 H H 507 Ir 2 1 Ph P1 CF3 FCF3 H H H H H CH3 H H 508 Ir 2 1 Ph P1 CH3 CF3 CH3 H H H H H CH3 H H 509Ir 2 1 Ph P1 C4H9 F C4H9 H H H H H CH3 H H 510 Ir 2 1 Ph P1 CH3 C2H5 CH3H H H H H CH3 H H 511 Ir 2 1 Ph P1 CH3 H CH3 H H H H H H CH3 H 512 Ir 21 Ph P1 CH3 CH3 H H H H H H CH3 H 513 Ir 2 1 Ph P1 CH3 F CH3 H H H H H HCH3 H 514 Ir 2 1 Ph P1 CF3 CH3 CF3 H H H H H H CH3 H 515 Ir 2 1 Ph P1CF3 F CF3 H H H H H H CH3 H 516 Ir 2 1 Ph P1 CH3 CF3 CH3 H H H H H H CH3H 517 Ir 2 1 Ph P1 C4H9 F C4H9 H H H H H H CH3 H 518 Ir 2 1 Ph P1 CH3C2H5 CH3 H H H H H H CH3 H 519 Ir 2 1 Ph P1 CH3 H CH3 H CF3 F H H CH3 HH 520 Ir 2 1 Ph P1 CH3 CH3 CH3 H CF3 F H H CH3 H H 521 Ir 2 1 Ph P1 CH3F CH3 H CF3 F H H CH3 H H 522 Ir 2 1 Ph P1 CF3 CH3 CF3 H CF3 F H H CH3 HH 523 Ir 2 1 Ph P1 CF3 F CF3 H CF3 F H H CH3 H H 524 Ir 2 1 Ph P1 CH3CF3 CH3 H CF3 F H H CH3 H H 525 Ir 2 1 Ph P1 C4H9 F C4H9 H CF3 F H H CH3H H 526 Ir 2 1 Ph P1 CH3 C2H5 CH3 H CF3 F H H CH3 H H 527 Ir 2 1 Ph P1CH3 H CH3 F H F H H H CH3 H 528 Ir 2 1 Ph P1 CH3 CH3 CH3 F H F H H H CH3H 529 Ir 2 1 Ph P1 CH3 F CH3 F H F H H H CH3 H 530 Ir 2 1 Ph P1 CF3 CH3CF3 F H F H H H CH3 H 531 Ir 2 1 Ph P1 CF3 F CF3 F H F H H H CH3 H 532Ir 2 1 Ph P1 CH3 CF3 CH3 F H F H H H CH3 H 533 Ir 2 1 Ph P1 C4H9 F C4H9F H F H H H CH3 H 534 Ir 2 1 Ph P1 CH3 C2H5 CH3 F H F H H H CH3 H 535 Ir2 1 Ph P1 CH3 H CH3 H F H F H H H H 536 Ir 2 1 Ph P1 CH3 CH3 CH3 H F H FH H H H 537 Ir 2 1 Ph P1 CH3 F CH3 H F H F H H H H 538 Ir 2 1 Ph P1 CF3CH3 CF3 H F H F H H CH3 H 539 Ir 2 1 Ph P1 CF3 F CF3 H H F H H H CF3 H540 Ir 2 1 Ph P1 CH3 CF3 CH3 H H F H H H CF3 H

[0091] TABLE 1-10 No M m n A B B′ or B″ E J G A-R1 A-R2 A-R3 A-R4 B-R5B-R6 B-R7 B-R8 541 Ir 2 1 Ph P1 — C4H9 F C4H9 H H F H H H CF3 H 542 Ir 21 Ph P1 — CH3 C2H5 CH3 H H F H H H CF3 H 543 Ir 2 1 Ph P1 — CH3 H CH3 HH F H H CF3 H H 544 Ir 2 1 Ph P1 — CH3 CH3 CH3 H H F H H CF3 H H 545 Ir2 1 Ph P1 — CH3 F CH3 H H F H H CF3 H H 546 Ir 2 1 Ph P1 — CF3 CH3 CF3 HH F H H CF3 H H 547 Ir 2 1 Ph P1 — CF3 F CF3 H H F H H CF3 H H 548 Ir 21 Ph P1 — CH3 CF3 CH3 H H F H H CF3 H H 549 Ir 2 1 Ph P1 — C4H9 F C4H9 HH F H H CF3 H H 550 Ir 2 1 Ph P1 — CH3 C2H5 CH3 H H F H H CF3 H H 551 Ir2 1 Ph P1 — CH3 H CH3 H CF3 F H H H H H 552 Ir 2 1 Ph P1 — CH3 CH3 CH3 HCF3 F H H H H H 553 Ir 2 1 Ph P1 — CH3 F CH3 H CF3 F H H H H H 554 Ir 21 Ph P1 — CF3 CH3 CF3 H CF3 F H H H H H 555 Ir 2 1 Ph P1 — CF3 F CF3 HCF3 F H H H H H 556 Ir 2 1 Ph P1 — CH3 CF3 CH3 H CF3 F H H H H H 557 Ir2 1 Ph P1 — C4H9 F C4H9 H CF3 F H H H H H 558 Ir 2 1 Ph P1 — CH3 C2H5CH3 H CF3 F H H H H H 559 Ir 2 1 Ph P1 — CH3 H CH3 H CF3 F H H H CH3 H560 Ir 2 1 Ph P1 — CH3 CH3 CH3 H CF3 F H H H CH3 H 561 Ir 2 1 Ph P1 —CH3 F CH3 H CF3 F H H H CH3 H 562 Ir 2 1 Ph P1 — CF3 CH3 CF3 H CF3 F H HH CH3 H 563 Ir 2 1 Ph P1 — CF3 F CF3 H CF3 F H H H CH3 H 564 Ir 2 1 PhP1 — CH3 CF3 CH3 H CF3 F H H H CH3 H 565 Ir 2 1 Ph P1 — C4H9 F C4H9 HCF3 F H H H CH3 H 566 Ir 2 1 Ph P1 — CH3 C2H5 CH3 H CF3 F H H H CH3 H567 Ir 2 1 Ph P1 — CH3 H CH3 H CF3 H CF3 H H H H 568 Ir 2 1 Ph P1 — CH3CH3 CH3 H CF3 H CF3 H H H H 569 Ir 2 1 Ph P1 — CH3 F CH3 H CF3 H CF3 H HH H 570 Ir 2 1 Ph P1 — CF3 CH3 CF3 H CF3 H CF3 H H H H 571 Ir 2 1 Ph P1— CF3 F CF3 H CF3 H CF3 H H H H 572 Ir 2 1 Ph P1 — CH3 CF3 CH3 H CF3 HCF3 H H H H 573 Ir 2 1 Ph P1 — C4H9 F C4H9 H CF3 H CF3 H H H H 574 Ir 21 Ph P1 — CH3 C2H5 CH3 H CF3 H CF3 H H H H 575 Ir 2 1 Ph P1 P1 — — — H HH H H H C4H9 H 576 Ir 2 1 Ph P1 P1 — — — F H H H H H C4H9 H 577 Ir 2 1Ph P1 P1 — — — H F H H H H C4H9 H 578 Ir 2 1 Ph P1 P1 — — — H H F H H HC4H9 H 579 Ir 2 1 Ph P1 P1 — — — H H H F H H C4H9 H 580 Ir 2 1 Ph P1 P1— — — F H F H H H C4H9 H 581 Ir 2 1 Ph P1 P1 — — — H F H F H H C4H9 H582 Ir 2 1 Ph P1 P1 — — — H F F H H H C4H9 H 583 Ir 2 1 Ph P1 P1 — — — FH H F H H C4H9 H 584 Ir 2 1 Ph P1 P1 — — — F F F F H H C4H9 H 585 Ir 2 1Ph P1 P1 — — — H CF3 H H H H C4H9 H 586 Ir 2 1 Ph P1 P1 — — — H H H CF3H H C4H9 H 587 Ir 2 1 Ph P1 P1 — — — H CF3 H CF3 H H C4H9 H 588 Ir 2 1Ph P1 P1 — — — H CF3 F H H H C4H9 H 589 Ir 2 1 Ph P1 P1 — — — F CF3 F HH H C4H9 H 590 Ir 2 1 Ph P1 P1 — — — F CF3 H H H H C4H9 H 591 Ir 2 1 PhP1 P1 — — — H H F CF3 H H C4H9 H 592 Ir 2 1 Ph P1 P1 — — — F H H CF3 H HC4H9 H 593 Ir 2 1 Ph P1 P1 — — — F H F CF3 H H C4H9 H 594 Ir 2 1 Ph P1P1 — — — H CH3 H H H H C4H9 H 595 Ir 2 1 Ph P1 P1 — — — H H CH3 H H HC4H9 H 596 Ir 2 1 Ph P1 P1 — — — H C2H5 H H H H C4H9 H 597 Ir 2 1 Ph P1P1 — — — H H C2H5 H H H C4H9 H 598 Ir 2 1 Ph P1 P1 — — — H C4H9 H H H HC4H9 H 599 Ir 2 1 Ph P1 P1 — — — H H C4H9 H H H C4H9 H 600 Ir 2 1 Ph P1P1 — — — F H H H H H H H

[0092] TABLE 1-11 No M m n A B B′ or B″ A-R1 A-R2 A-R3 A-R4 B-R5 B-R6B-R7 B-R8 601 Ir 2 1 Ph P1 P1 H F H H H H H H 602 Ir 2 1 Ph P1 P1 H H FH H H H H 603 Ir 2 1 Ph P1 P1 H H H F H H H H 604 Ir 2 1 Ph P1 P1 H F HF H H H H 605 Ir 2 1 Ph P1 P1 H F F H H H H H 606 Ir 2 1 Ph P1 P1 F H HF H H H H 607 Ir 2 1 Ph P1 P1 F F F F H H H H 608 Ir 2 1 Ph P1 P1 H CF3H H H H H H 609 Ir 2 1 Ph P1 P1 H H H CF3 H H H H 610 Ir 2 1 Ph P1 P1 HCF3 H CF3 H H H H 611 Ir 2 1 Ph P1 P1 H CF3 F H H H H H 612 Ir 2 1 Ph P1P1 F CF3 F H H H H H 613 Ir 2 1 Ph P1 P1 F CF3 H H H H H H 614 Ir 2 1 PhP1 P1 H H F CF3 H H H H 615 Ir 2 1 Ph P1 P1 F H H CF3 H H H H 616 Ir 2 1Ph P1 P1 F H F CF3 H H H H 617 Ir 2 1 Ph P1 P1 H CH3 H H H H H H 618 Ir2 1 Ph P1 P1 H H CH3 H H H H H 619 Ir 2 1 Ph P1 P1 H C2H5 H H H H H H620 Ir 2 1 Ph P1 P1 H H C2H5 H H H H H 621 Ir 2 1 Ph P1 P1 H C4H9 H H HH H H 622 Ir 2 1 Ph P1 P1 H H C4H9 H H H H H 623 Ir 2 1 Ph P1 P1 H H H HH H H CH3 624 Ir 2 1 Ph P1 P1 F H H H H H H CH3 625 Ir 2 1 Ph P1 P1 H FH H H H H CH3 626 Ir 2 1 Ph P1 P1 H H F H H H H CH3 627 Ir 2 1 Ph P1 P1H H H F H H H CH3 628 Ir 2 1 Ph P1 P1 F H F H H H H CH3 629 Ir 2 1 Ph P1P1 H F H F H H H CH3 630 Ir 2 1 Ph P1 P1 H F F H H H H CH3 631 Ir 2 1 PhP1 P1 F H H F H H H CH3 632 Ir 2 1 Ph P1 P1 F F F F H H H CH3 633 Ir 2 1Ph P1 P1 H CF3 H H H H H CH3 634 Ir 2 1 Ph P1 P1 H H H CF3 H H H CH3 635Ir 2 1 Ph P1 P1 H CF3 H CF3 H H H CH3 636 Ir 2 1 Ph P1 P1 H CF3 F H H HH CH3 637 Ir 2 1 Ph P1 P1 F CF3 F H H H H CH3 638 Ir 2 1 Ph P1 P1 F CF3H H H H H CH3 639 Ir 2 1 Ph P1 P1 H H F CF3 H H H CH3 640 Ir 2 1 Ph P1P1 F H H CF3 H H H CH3 641 Ir 2 1 Ph P1 P1 F H F CF3 H H H CH3 642 Ir 21 Ph P1 P1 H CH3 H H H H H CH3 643 Ir 2 1 Ph P1 P1 H H CH3 H H H H CH3644 Ir 2 1 Ph P1 P1 H C2H5 H H H H H CH3 645 Ir 2 1 Ph P1 P1 H H C2H5 HH H H CH3 646 Ir 2 1 Ph P1 P1 H C4H9 H H H H H CH3 647 Ir 2 1 Ph P1 P1 HH C4H9 H H H H CH3 648 Ir 3 0 Ph P2 — H H CH3 H H H H — 649 Ir 3 0 Ph P2— H H C4H9 H H H H — 650 Ir 3 0 Ph P2 — F H F H H H H — 651 Ir 3 0 Ph P2— H H F H H H H — 652 Ir 3 0 Ph P2 — H CF3 H H H H H — 653 Ir 3 0 Ph P2— H H H H H H H — 654 Ir 3 0 Ph P2 — H H H H H H H — 655 Ir 3 0 Ph P2 —H H H H H H H — 656 Ir 3 0 Ph P2 — H H H H H H CH3 — 657 Ir 3 0 Ph P2 —H H H H H CH3 H — 658 Ir 3 0 Ph P3 — H H CH3 H H H H — 659 Ir 3 0 Ph P3— H H C4H9 H H H H — 660 Ir 3 0 Ph P3 — F H F H H H H —

[0093] TABLE 1-12 No M m n A B A-R1 A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8661 Ir 3 0 Ph P3 H H F H H H H — 662 Ir 3 0 Ph P3 H CF3 H H H H H — 663Ir 3 0 Ph P3 H H H H H H H — 664 Ir 3 0 Ph P3 H H H H H H H — 665 Ir 3 0Ph P3 H H H H H H H — 666 Ir 3 0 Ph P3 H H H H CH3 H H — 667 Ir 3 0 PhP3 H H H H H CH3 H — 668 Ir 3 0 Ph P4 H H CH3 H H H H — 669 Ir 3 0 Ph P4H H C4H9 H H H H — 670 Ir 3 0 Ph P4 F H F H H H H — 671 Ir 3 0 Ph P4 H HF H H H H — 672 Ir 3 0 Ph P4 H CF3 H H H H H — 673 Ir 3 0 Ph P4 H H H HH H H — 674 Ir 3 0 Ph P4 H H H H H H H — 675 Ir 3 0 Ph P4 H H H H H H H— 676 Ir 3 0 Ph P4 H H H H CH3 H H — 677 Ir 3 0 Ph P4 H H H H H CH3 H —678 Ir 3 0 Ph P5 H H CH3 H H H H — 679 Ir 3 0 Ph P5 H H C4H9 H H H H —680 Ir 3 0 Ph P5 H H F H H H H — 681 Ir 3 0 Ph P5 H CF3 H H H H H — 682Ir 3 0 Ph P5 H H H H H CH3 H — 683 Ir 3 0 Ph P6 H H CH3 H H H H H 684 Ir3 0 Ph P6 H H C4H9 H H H H H 685 Ir 3 0 Ph P6 H H F H H H H H 686 Ir 3 0Ph P6 H CF3 H H H H H H 687 Ir 3 0 Ph P6 H H H H H CH3 H H 688 Ir 3 0 PhP7 H H CH3 H H H H H 689 Ir 3 0 Ph P7 H H C4H9 H H H H H 690 Ir 3 0 PhP7 H H F H H H H H 691 Ir 3 0 Ph P7 H CF3 H H H H H H 692 Ir 3 0 Ph P7 HH H H H CH3 H H 693 Ir 3 0 Ph P8 H H CH3 H H H H H 694 Ir 3 0 Ph P8 H HC4H9 H H H H H 695 Ir 3 0 Ph P8 H H F H H H H H 696 Ir 3 0 Ph P8 H H H HH H CH3 H 697 Ir 3 0 Ph P8 H H H H H CH3 H H 698 Ir 3 0 Ph P9 H H CH3 HH H H H 699 Ir 3 0 Ph P9 H H C4H9 H H H H H 700 Ir 3 0 Ph P9 H H F H H HH H 701 Ir 3 0 Ph P9 H H H H H H CH3 H 702 Ir 3 0 Ph P9 H H H H H CH3 HH

[0094] TABLE 1-13 No M m n A B A′ B′ or B″ E J G A-R1 A-R2 A-R3 703 Ir 21 Ph P1 Ph P1 — — — H H H 704 Ir 2 1 Ph P1 Tn1 P1 — — — H H CH3 705 Ir 21 Ph P1 Tn1 P6 — — — H H H 706 Ir 2 1 Ph P1 Tn1 P8 — — — H H CH3 707 Ir2 1 Ph P1 Tn2 P1 — — — H H H 708 Ir 2 1 Ph P1 Tn3 P1 — — — H H CH3 709Ir 2 1 Ph P1 Np1 P1 — — — H H H 710 Ir 2 1 Ph P1 Np2 P1 — — — H H CH3711 Ir 2 1 Ph P1 Np2 P6 — — — H H H 712 Ir 2 1 Ph P1 Np2 P8 — — — H H H713 Ir 2 1 Ph P1 Pe P1 — — — H H H 714 Ir 2 1 Ph P1 Cn1 P1 — — — H H H715 Ir 2 1 Ph P1 Cn2 P1 — — — H H H 716 Ir 2 1 Ph P1 FI P1 — — — H H H717 Ir 2 1 Ph P1 FI P1 — — — H H CH3 718 Ir 2 1 Ph P1 FI P6 — — — H HCH3 719 Ir 2 1 Ph P1 FI P8 — — — H H CH3 720 Ir 2 1 Ph P1 Qn1 P1 — — — HH H 721 Ir 2 1 Ph P1 Cz P1 — — — H H CH3 722 Ir 2 1 Ph P1 Fn1 P1 — — — HH CH3 723 Ir 3 0 Tn1 P1 — — — — — CH3 H — 724 Ir 3 0 Tn1 P1 — — — — —C2H5 H — 725 Ir 3 0 Tn1 P1 — — — — — C4H9 H — 726 Ir 3 0 Tn1 P1 — — — —— F H — 727 Ir 3 0 Tn1 P1 — — — — — CF3 H — 728 Ir 3 0 Tn1 P1 — — — — —H CH3 — 729 Ir 3 0 Tn1 P1 — — — — — H H — 730 Ir 3 0 Tn1 P1 — — — — —CH3 H — 731 Ir 3 0 Tn1 P1 — — — — — H H — 732 Ir 3 0 Tn1 P6 — — — — —CH3 H — 733 Ir 2 1 Tn1 P1 — — CH3 CH3 CH3 H H — 734 Ir 2 1 Tn1 P5 — —CH3 H CH3 CH3 H — 735 Ir 3 0 Tn2 P1 — — — — — H CF3 — 736 Ir 3 0 Tn2 P1— — — — — H CF3 — 737 Ir 3 0 Tn2 P1 — — — — — H CF3 — 738 Ir 3 0 Tn2 P1— — — — — H CF3 — 739 Ir 3 0 Tn2 P1 — — — — — H H — 740 Ir 2 1 Tn2 P1 —— CH3 F CH3 H H — 741 Ir 2 1 Tn2 P1 — P1 — — — H CH3 — 742 Ir 2 1 Tn2 P1— P1 — — — H H — 743 Ir 2 1 Tn2 P1 — P1 — — — H H — No A-R4 A′-R1 A′-R2A′-R3 A′-R4 B-R5 B-R6 B-R7 B-R8 B′-R5 B′-R6 B′-R7 B′-R8 703 H H H CH3 HH H H H H H H H 704 H H H — — H H H H H H H H 705 H CH3 H — — H H H H HH H H 706 H H H — — H H H H H H H H 707 H H CH3 — — H H H H H H H H 708H H H H H H H H H H H H H 709 H CH3 H H H H H H H H H H H 710 H H H H HH H H H H H H H 711 H H H H H H CH3 H H H H H H 712 H H H H H H H CH3 HH H H H 713 H H H H H H H H H H H H H 714 H H H — — H H H H H H H H 715H H H — — H H H H H H H H 716 H H H Ph H H H H H H H H H 717 H H H H H HH H H H H H H 718 H H H H H H H H H H H H H 719 H H H H H H H H H H H HH 720 H CH3 H H — H H H H H H H H 721 H H H H H H H H H H H H H 722 H HH H H H H H H H H H H 723 — — — — — H H H H — — — — 724 — — — — — H H HH — — — — 725 — — — — — H H H H — — — — 726 — — — — — H H H H — — — —727 — — — — — H H H H — — — — 728 — — — — — H H H H — — — — 729 — — — —— H H CF3 H — — — — 730 — — — — — H H CF3 H — — — — 731 — — — — — H HCH3 H — — — — 732 — — — — — H H H H — — — — 733 — — — — — H H H H — — —— 733 — — — — — H H H H — — — — 734 — — — — — H H H H — — — — 735 — — —— — H H H H — — — — 736 — — — — — H H H H — — — — 737 — — — — — H H CH3H — — — — 738 — — — — — H H H CH3 — — — — 739 — — — — — H H CH3 H — — —— 740 — — — — — H H H H — — — — 741 — — — — — H H H H H H H H 742 — — —— — H H H H H H C4H9 H 743 — — — — — H H CH3 H H H H H

[0095] TABLE 1-14 No M m n A B B′ or B″ E J G A-R1 A-R2 A-R3 A-R4 B-R5B-R6 B-R7 B-R8 B′-R5 B′-R6 B′-R7 B′-R8 744 Ir 3 0 Tn3 P1 — — — — H H H HH H CH3 H — — — — 745 Ir 3 0 Tn3 P1 — — — — H H H H H CH3 H H — — — —746 Ir 3 0 Tn3 P1 — — — — H H H H H H CF3 H — — — — 747 Ir 3 0 Tn3 P1 —— — — H H H H H H CF3 H — — — — 748 Ir 2 1 Tn3 P1 — CH3 CH3 CH3 H H H HH H H H — — — — 749 Ir 2 1 Tn3 P1 — CH3 H CH3 H H H H H H CF3 H — — — —750 Ir 2 1 Tn3 P1 — CH3 F CH3 H H H H H H H H — — — — 751 Ir 3 0 Np1 P1— — — — CH3 H H H H H H H — — — — 752 Ir 3 0 Np1 P1 — — — — CH3 H H H HCH3 H H — — — — 753 Ir 3 0 Np1 P1 — — — — CH3 H H H H H CH3 H — — — —754 Ir 3 0 Np1 P1 — — — — CH3 H H H H CF3 H H — — — — 755 Ir 3 0 Np1 P1— — — — CH3 H H H H H CF3 H — — — — 756 Ir 3 0 Np1 P1 — — — — F H H H HH H H — — — — 757 Ir 3 0 Np1 P1 — — — — CF3 H H H H H H H — — — — 758 Ir3 0 Np1 P1 — — — — Ph H H H H H H H — — — — 759 Ir 3 0 Np1 P1 — — — — FH H H H H CF3 H — — — — 760 Ir 2 1 Np1 P1 — CH3 H CH3 CH3 H H H H H H H— — — — 761 Ir 2 1 Np1 P1 — CH3 CH3 CH3 CH3 H H H H H H H — — — — 762 Ir2 1 Np1 P1 — CH3 F CH3 CH3 H H H H H H H — — — — 763 Ir 2 1 Np1 P1 — CH3C2H5 CH3 CH3 H H H H H H H — — — — 764 Ir 2 1 Np1 P1 — CH3 H CH3 CH3 H HH H H CF3 H — — — — 765 Ir 2 1 Np1 P1 P1 — — — CH3 H H H H H H H H H H H766 Ir 2 1 Np1 P1 P1 — — — CH3 H H H H H CF3 H H H H H 767 Ir 3 0 Np2 P1— — — — H H H H H H CH3 H — — — — 768 Ir 3 0 Np2 P1 — — — — H H H H HCH3 H H — — — — 769 Ir 3 0 Np2 P1 — — — — H CH3 H H H H H H — — — — 770Ir 3 0 Np2 P1 — — — — H H CH3 H H H H H — — — — 771 Ir 3 0 Np2 P1 — — —— H H F H H H H H — — — — 772 Ir 2 1 Np2 P1 — CH3 CH3 CH3 H H H H H H HH — — — — 773 Ir 2 1 Np2 P6 — CH3 H CH3 H H CH3 H H H H H — — — — 774 Ir3 0 Pe P1 — — — — H H H H H CH3 H H — — — — 775 Ir 3 0 Pe P1 — — — — H HH H H H CH3 H — — — — 776 Ir 3 0 Pe P1 — — — — H H H H CH3 H H H — — — —777 Ir 3 0 Pe P1 — — — — H H H H H H CF3 H — — — — 778 Ir 2 1 Pe P1 —CH3 H CH3 H H H H H H H H — — — — 779 Ir 2 1 Pe P1 P1 — — — H H H H H HCH3 H H H H H 780 Ir 3 0 FI P1 — — — — H H CH3 H H H H H — — — —

[0096] TABLE 1-15 B′ No M m n A B or B″ E J G A-R1 A-R2 A-R3 A-R4 B-R5B-R6 B-R7 B-R8 B′-R5 B′-R6 B′-R7 B′-R8 781 Ir 3 0 FI P1 — — — — H H C2H5H H H H H — — — — 782 Ir 3 0 FI P1 — — — — H H H H H H CH3 H — — — — 783Ir 3 0 FI P1 — — — — H H H H H CH3 H H — — — — 784 Ir 3 0 FI P1 — — — —H H CH3 H H H CH3 H — — — — 785 Ir 3 0 FI P6 — — — — H H Ph H H H H H —— — — 786 Ir 3 0 FI P6 — — — — H H CH3 H H H H H — — — — 787 Ir 2 1 FIP1 — CH3 H CH3 H H CH3 H H H H H — — — — 788 Ir 2 1 FI P1 — CH30 CH3 CH3H H H H H H H H — — — — 789 Ir 2 1 FI P6 — CH3 H CH3 H H CH3 H H H H H —— — — 790 Ir 2 1 FI P6 — CH30 CH3 CH3 H H H H H H H H — — — — 791 Ir 3 0Qn1 P1 — — — — H H CH3 H H H H H — — — — 792 Ir 3 0 Qn1 P3 — — — — H HCH3 H H H H H — — — — 793 Ir 3 0 Qn2 P1 — — — — H CH3 H H H H H H — — —— 794 Ir 3 0 Qn2 P8 — — — — H CH3 H H H H H H — — — — 795 Ir 3 0 Cz P1 —— — — H CH3 H H H H H H — — — — 796 Ir 3 0 Cz P1 — — — — H C2H5 H H H HH H — — — — 797 Ir 3 0 Cz P1 — — — — H C4H9 H H H H H H — — — — 798 Ir 30 Cz P1 — — — — H C8H17 H H H H H H — — — — 799 Ir 3 0 Cz P1 — — — — HCH3 H CH3 H H H H — — — — 800 Ir 3 0 Cz P1 — — — — H C2H5 H CH3 H H H H— — — — 801 Ir 3 0 Cz P1 — — — — H CH3 H H H CH3 H H — — — — 802 Ir 3 0Cz P1 — — — — H CH3 H H H H CH3 H — — — — 803 Ir 3 0 Cz P1 — — — — H PhH H H H H H — — — — 804 Ir 3 0 Cz P6 — — — — H CH3 H H H H H H — — — —805 Ir 2 1 Cz P1 — CH3 H CH3 H CH3 H H H H H H — — — — 806 Ir 2 1 Cz P1— CH30 CH3 CH3 H CH3 H H H H H H — — — — 807 Ir 2 1 Cz P1 — CH3 F CH3 HCH3 H H H H H H — — — — 808 Ir 2 1 Cz P1 P1 — — — H CH3 H H H H H H H HH H 809 Ir 3 0 Fn1 P1 — — — — H H H H H H CH3 H — — — — 810 Ir 3 0 Fn1P1 — — — — H H H H H CH3 H H — — — — 811 Ir 3 0 Fn1 P1 — — — — H H H HCH3 H H H — — — — 812 Ir 3 0 Fn1 P3 — — — — H H H H H H CH3 — — — — —813 Ir 2 1 Fn1 P1 — CH3 H CH3 H H H H H H CH3 H — — — — 814 Ir 2 1 Fn1P1 — CH30 CH3 CH3 H H H H H H H H — — — — 815 Ir 2 1 Fn1 P1 — CH3 F CH3H H H H H H H H — — — — 816 Ir 2 1 Fn1 P1 P1 — — — H H H H H H C4H9 H —— — — 817 Rh 3 0 Ph P1 — — — — H H CH3 H H H H H — — — — 818 Rh 3 0 PhP1 — — — — H CH3 H H H H H H — — — — 819 Rh 3 0 Ph P1 — — — — H H C2H5 HH H H H — — — — 820 Rh 3 0 Ph P1 — — — — H H C2H9 H H H H H — — — —

[0097] TABLE 1-16 B′- B′- B′- B′- No M m n A B B′ or B″ E J G A-R1 A-R2A-R3 A-R4 B-R5 B-R6 B-R7 B-R8 R5 R6 R7 R8 821 Rh 3 0 Ph P1 — — — — H CF3H H H H H H — — — — 822 Rh 3 0 Ph P1 — — — — H H F H H H H H — — — — 823Rh 3 0 Ph P1 — — — — F H F H H H H H — — — — 824 Rh 3 0 Ph P1 — — — — HCF3 F H H H H H — — — — 825 Rh 3 0 Ph P1 — — — — H CF3 H CF3 H H H H — —— — 826 Rh 3 0 Ph P1 — — — — F CF3 F H H H H H — — — — 827 Rh 3 0 Ph P1— — — — H CF3 H H H H CH3 H — — — — 828 Rh 3 0 Ph P6 — — — — H CH3 H H HH H H — — — — 829 Rh 3 0 Fl P1 — — — — H H H H H CH3 H H — — — — 830 Rh3 0 Fl P1 — — — — H H H H H H CH3 H — — — — 831 Rh 2 1 Ph P1 — CH3 H CH3H H F H H H H H — — — — 832 Rh 2 1 Ph P1 — CH30 CH3 CH3 H H F H H H H H— — — — 833 Rh 2 1 Ph P1 — CH3 F CH3 H H F H H H H H — — — — 834 Rh 2 1Ph P1 P1 — — — H H F H H H H H H H H H 835 Rh 2 1 Ph P1 P1 — — — F H F HH H H H H H H H 836 Pt 2 0 Ph P1 — — — — H CH3 H H H H H H — — — — 837Pt 2 0 Ph P1 — — — — H H CH3 H H H H H — — — — 838 Pt 2 0 Ph P1 — — — —H C2H5 H H H H H H — — — — 839 Pt 2 0 Ph P1 — — — — H H C2H5 H H H H H —— — — 840 Pt 2 0 Ph P1 — — — — H H C4H9 H H H H H — — — — 841 Pt 2 0 PhP1 — — — — H H C8H17 H H H H H — — — — 842 Pt 2 0 Ph P1 — — — — H HC16H33 H H H H H — — — — 843 Pt 2 0 Ph P1 — — — — H H CH3O H H H H H — —— — 844 Pt 2 0 Ph P1 — — — — H H C2H5O H H H H H — — — — 845 Pt 2 0 PhP1 — — — — H C2H4O H H H H H H — — — — 846 Pt 2 0 Ph P1 — — — — H CF3 HH H H H H — — — — 847 Pt 2 0 Ph P1 — — — — H H F H H H H H — — — — 848Pt 2 0 Ph P1 — — — — H CF3 F H H H H H — — — — 849 Pt 2 0 Ph P1 — — — —H CF3 H CF3 H H H H — — — — 850 Pt 2 0 Ph P1 — — — — F H F H H H H H — —— — 851 Pt 2 0 Ph P1 — — — — F CF3 F H H H H H — — — — 852 Pt 2 0 Ph P1— — — — H CF3 F CF3 H H H H — — — — 853 Pt 2 0 Ph P1 — — — — H H CH3 H HH CH3 H — — — — 854 Pt 2 0 Ph P1 — — — — H C2H5 H H H H CH3 H — — — —855 Pt 2 0 Ph P1 — — — — H H C2H5 H H H CH3 H — — — — 856 Pt 2 0 Ph P1 —— — — H H C4H9 H H H CH3 H — — — — 857 Pt 2 0 Ph P1 — — — — H H C8H17 HH H CH3 H — — — — 858 Pt 2 0 Ph P1 — — — — H H C16H33 H H H CH3 H — — —— 859 Pt 2 0 Ph P1 — — — — H H CH3O H H H CH3 H — — — — 860 Pt 2 0 Ph P1— — — — H H C2H5O H H H CH3 H — — — —

[0098] TABLE 1-17 B′- B′- B′- B′- No M m n A B A′ B′ or B″ E J G A-R1A-R2 A-R3 A-R4 B-R5 B-R6 B-R7 B-R8 R5 R6 R7 R8 861 Pt 2 0 Ph P1 — — — —— H C2H4O H H H H CH3 H — — — — 862 Pt 2 0 Ph P1 — — — — — H CF3 H H H HCH3 H — — — — 863 Pt 2 0 Ph P1 — — — — — H H F H H H CH3 H — — — — 864Pt 2 0 Ph P1 — — — — — H CF3 F H H H CH3 H — — — — 865 Pt 2 0 Ph P1 — —— — — H CF3 H CF3 H H CH3 H — — — — 866 Pt 2 0 Ph P1 — — — — — F H F H HH CH3 H — — — — 867 Pt 2 0 Ph P1 — — — — — F CF3 F H H H CH3 H — — — —868 Pt 2 0 Ph P1 — — — — — H CF3 F CF3 H H CH3 H — — — — 869 Pt 1 1 PhP1 — — CH3 H CH3 H CH3 H H H H H H — — — — 870 Pt 1 1 Ph P1 — — CH3 CH3CH3 H H F H H H H H — — — — 871 Pt 1 1 Ph P1 — — CH3 F CH3 F H F H H H HH — — — — 872 Pt 1 1 Ph P1 — — CH3 F CH3 H CF3 F H H H H H — — — — 873Pt 1 1 Ph P1 — P1 — — — H CF3 F H H H H H H H C4H9 H 874 Pt 1 1 Ph P1 —P1 — — — H CF3 F H H H H H — — — — 875 Pt 1 1 Ph P1 Tn1 P1 — — — CH3 H HH H H H H — — — — 876 Pt 1 1 Ph P1 Np1 P1 — — — CH3 H H H H H H H — — —— 877 Pd 2 0 Ph P1 — — — — — H H CH3 H H H H H — — — — 878 Pd 2 0 Ph P1— — — — — H H C2H5 H H H H H — — — — 879 Pd 2 0 Ph P1 — — — — — H H F HH H H H — — — — 880 Pd 2 0 Ph P6 — — — — — H CF3 F H H H H H — — — — 881Pd 2 0 Cz P1 — — — — — H CH3 H H H H H H — — — — 882 Pd 1 1 Ph P1 — —CH3 H CH3 H H H H H H H H — — — — 883 Pd 1 1 Ph P1 — P1 — — — H H CH3 HH H H H — — — —

[0099] Hereinbelow, the present invention will be described morespecifically based on Examples.

[0100] Iridium metal coordination compounds used in Examples weresynthesized along synthesis paths shown below. (Analogous reactions aredescribed in Inorg. Chem. 1994, 33, p. 545).

[0101] <<Synthesis of iridium metal coordination compounds>>

[0102] A process scheme for synthesizing iridium complexes used in thepresent invention is shown below.

EXAMPLE 1

[0103] Synthesis of Example Compound No. 729

[0104] In a 100 mi-three-necked flask, 3.18 g (24.9 mmol) ofthienylboronic acid, 5.65 g (25.0 mmol) of1-bromo-4-trifluoromethylpyridine, 25 m of toluene, 12.5 ml of ethanoland 25 ml of 2M-sodium carbonate aqueous solution, were placed andstirred at room temperature under a nitrogen stream, followed byaddition of 0.98 g (0.85 mmol) of tetrakis(triphenylphosphine)palladium(0). Thereafter, the system was refluxed under stirring and nitrogenstream for 8 hours. After completion of the reaction, the reactionproduct was cooled and extracted by adding cold water and toluene. Theorganic layer was washed with saline water and dried on magnesiumsulfate, followed by removal of the solvent under a reduced pressure toprovide dry solid. The residue was purified by silica gel columnchromatography (eluent: chloroform/methanol=10/1) to obtain 4.20 g(yield=74%) of Compound A.

[0105] In a 100 ml-four-necked flask, 50 ml of glycerol was placed andheated for 2 hours at 130-140° C. under stirring and bubbling withnitrogen. The glycerol was cooled to room temperature and poured into300 ml of 1N-hydrochloric acid, and the precipitate was filtered out andwashed with water. The precipitate was then purified by silica gelchromatography with chloroform as eluent, to obtain 0.33 g (yield: 38%)of red powdery Example Compound No. 729.

[0106] A toluene solution of the compound exhibited a luminescencespectrum showing λmax=563 nm. The compound was subjected to MALDI-TOF(matrix-assisted laser desorption ionization time-of-flight massspectroscopy) by using an apparatus (“REFLEX-III”, made by Bruker Co.).In the method, an ion obtained by removing one electron from a samplesubstance is subjected to measurement of a mass thereof, so that themeasured mass is denoted by M⁺, and the method is frequently used foridentification of a substance. The measured M⁺ value was 877.0 fromwhich the objective product was confirmed.

[0107] For confirmation of phosphorescence-type luminescence, theExample Compound was dissolved in chloroform, and the solution wasseparately aerated with oxygen or nitrogen, each followed byphotoirradiation for comparison of photoluminescence. As a result,substantially no luminescence attributable to the iridium complex wasrecognized with respect to the oxygen-aerated solution, whereasphotoluminescence was confirmed with respect to the nitrogen-aeratedsolution. From these results, the compound of the present invention wasconfirmed to be a phosphorescent compound. For reference, in the case ofa fluorescent material, luminescence attributable to the compound doesnot disappear even in an oxygen aerated solution.

[0108] Further, in contrast with a fluorescent material generallyshowing a luminescence life of several nsec to several tens of nsec, thecompounds of the present invention including those obtained in thefollowing Examples, all exhibited a phosporescence life of 100 nsec orlonger.

EXAMPLE 2

[0109] Example Compound No. 310 was synthesized through a similarprocess as in Example 1.

[0110] Luminescence of toluene solution: λmax=489 nm MALDI-TOF MS:M⁺=859.1

EXAMPLE 3

[0111] Example Compound No. 238 was synthesized through a similarprocess as in Example 1.

[0112] Luminescence of toluene solution: λmax=515 nm MALDI-TOF MS:M⁺=709.1

EXAMPLE 4

[0113] Example Compound No. 242 was synthesized through a similarprocess as in Example 1.

[0114] Luminescence of toluene solution: λmax=471 nm MALDI-TOF MS:M⁺=763.1

EXAMPLE 5

[0115] Example Compound No. 384 was synthesized through a similarprocess as in Example 1.

[0116] Luminescence of toluene solution: λmax=466 nm MALDI-TOF MS:M⁺=913.1

EXAMPLE 6

[0117] Example Compound No. 777 was synthesized through a similarprocess as in Example 1.

[0118] Luminescence of toluene solution: max=696 nm MALDI-TOF MS:M⁺=1231.1

EXAMPLE 7

[0119] Example Compound No. 472 was synthesized.

[0120] In a 100 ml-two-necked flask, 60 ml of ethoxyethanol and 20 ml ofH₂O were placed and stirred for 1 hour under bubbling with nitrogen.Then, 0.51 g (4.4 mmol) of Compound C and 0.71 g (2.0 mmol) of iridium(III) trichloride hydrate were added, and the system was heated for 16hours around 100° C. under stirring and nitrogen stream. The reactionproduct was cooled to room temperature and poured into 100 ml of water,followed by recovery by filtration and washing with water of theprecipitate. The precipitate was then poured into 60 ml of ethanol andstirred for 1 hour, followed by filtering-out and washing with acetone,to obtain 0.95 g (yield: 89%) of yellow powdery Compound D.

[0121] In a 100 ml-two-necked flask, 50 ml of ethoxyethanol was placedand stirred for 1 hour under bubbling with nitrogen. Then, 0.536 g (0.5mmol) of Compound D, 0.17 g (1.4 mmol) of Compound E and 0.75 g ofsodium carbonate Na₂CO₃ were added, and the system was heated for 16hours around 100° C. under stirring and nitrogen stream. The reactionproduct was cooled to room temperature and poured into 100 ml of water,followed by filtering-out and washing with water of the precipitate. Theprecipitate was poured into 70 ml of ethanol, and after stirring for 1hour, the precipitate was filtered out and dissolved in chloroform,followed by filtration. The resultant filtrate was condensed, andpurified by silica gel column chromatography with chloroform as eluentto obtain 0.45 g (yield: 73%) of yellow powdery Example Compound No.472. A toluene solution of the compound exhibited a luminescencespectrum showing λmax=526 nm. The compound exhibited M⁺=614.2 accordingto MALDI-TOF MS and was confirmed to be the objective product.

EXAMPLE 8

[0122] In this Example, a device (effective display area=3 mm²) having adevice structure including 4 organic layers as shown in FIG. 1(c) wasprepared. An alkali-free glass sheet was used as a transparent substrate15 and a 100 nm-thick indium tin oxide (ITO) film was formed bysputtering and patterned as a transparent electrode 14. Further, α-NPDrepresented by the above-mentioned structural formula wasvacuum-deposited in a layer thickness of 40 nm thereon as ahole-transporting layer 13. Then, as an organic luminescence layer 12,the above-mentioned CBP as a host material and Example Compound No. 729(metal coordination compound) in an amount of providing 8 wt. % wereco-vacuum deposited in a layer thickness of 30 nm. Further, as anexciton diffusion-prevention layer 17, BCP was vacuum-deposited in athickness of 10 nm. Then, as an electron-transporting layer 16, theabove-mentioned Alq3 was subjected to resistance heating vacuumdeposition at a vacuum of 10⁻⁴ Pa to form an organic film in a thicknessof 30 nm.

[0123] On the above, as a lower layer of a metal electrode layer 11, anAlLi alloy film was disposed in a thickness of 15 nm, and a 100 nm-thickAl film was vacuum-deposited thereon to form a patterned metal electrode11 disposed opposite to the transparent electrode 14 and having anelectrode area of 3 mm2

[0124] The performances of the thus-obtained EL device were measured byusing a micro-current meter (“4140B”, made by Hewlett-Packard Corp.) fora current-voltage characteristic and “BM7” (made by Topcon K.K.) for anemission luminance.

EXAMPLE 9

[0125] A device was prepared in the same manner as in Example 8 exceptusing a metal coordination compound (Example Compound No. 729) was usedin a weight ratio of 7 wt. %.

COMPARATIVE EXAMPLE 1

[0126] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (729R) shown in Table 2 (whereina substituted compound of the present invention to be compared therewithis shown in parallel) in a weight ratio of 8 wt. %. TABLE 2 A- A- A- A-B- B- B- B- No M N m A B R1 R2 R3 R4 R5 R6 R7 R8 729R Ir 3 0 Tn1 P1 H H— — H H H H 729 Ir 3 0 Tn1 P1 H H — — H H CF₃ H

COMPARATIVE EXAMPLE 2

[0127] A device was prepared in the same manner as in Example 8 exceptfor using the metal coordination compound (729R) shown in Table 2 in aweight ratio of 3 wt. %.

COMPARATIVE EXAMPLE 3

[0128] A device was prepared in the same manner as in Example 8 exceptfor using the metal coordination compound (729R) shown in Table 2 in aweight ratio of 1 wt. %.

[0129] Each device was supplied with an electric field of 12 volts/100nm with the ITO side as the anode and the Al side as the cathode tomeasure a luminance.

[0130] In order to remove factors for device deterioration due to oxygenor water, the above-measurement was performed in a dry nitrogen flowafter taking the device out of the vacuum chamber.

[0131] The results of devices using the respective compounds are shownin Table 3. As is understood from the results shown in Table 3, themaximum luminance concentration of Comparative Compound 729R was clearlybetween 1% and 8%, whereas Example Compound No. 729 provided with asubstituent exhibited a higher luminance at 8% than at 7% and couldexhibit a substantially higher luminance at 8% than 729R having nosubstituent. TABLE 3 <Luminance comparison> Concentration LuminanceExample Compound No. (wt. %) (cd/m²) 8 729 8 4500 9 729 7 4250 Comp. 1729R 8 1620 Comp. 2 729R 3 4000 Comp. 3 729R 1 1290

EXAMPLE 10

[0132] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (310) synthesized in Example 2in a weight ratio of 3 wt. %.

EXAMPLE 11

[0133] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (310) synthesized in Example 2in a weight ratio of 6 wt. %.

EXAMPLE 12

[0134] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (310) synthesized in Example 2in a weight ratio of 8 wt. %.

EXAMPLE 13

[0135] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (238) synthesized in Example 3in a weight ratio of 3 wt. %.

EXAMPLE 14

[0136] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (238) synthesized in Example 3in a weight ratio of 6 wt. %.

EXAMPLE 15

[0137] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (238) synthesized in Example 3in a weight ratio of 8 wt. %.

Example 15A

[0138] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (238) synthesized in Example 3in a weight ratio of 11 wt. %

Example 15B

[0139] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (238) synthesized in Example 3in a weight ratio of 13 wt. %.

EXAMPLE 16

[0140] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (242) synthesized in Example 4in a weight ratio of 3 wt. %.

EXAMPLE 17

[0141] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (242) synthesized in Example 4in a weight ratio of 6 wt. %.

EXAMPLE 18

[0142] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (242) synthesized in Example 4in a weight ratio of 8 wt. %.

EXAMPLE 19

[0143] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (384) synthesized in Example 5in a weight ratio of 3 wt. %.

EXAMPLE 20

[0144] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (384) synthesized in Example 5in a weight ratio of 6 wt. %.

EXAMPLE 21

[0145] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (384) synthesized in Example 5in a weight ratio of 8 wt. %.

COMPARATIVE EXAMPLE 4

[0146] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (1R) shown in Table 4 (whereinstructures of the corresponding Example Compound Nos. 310, 238, 242 and384 are shown in parallel) in a weight ratio of 3 wt. % TABLE 4 A- A- A-A- B- B- B- B- No M m n A B R1 R2 R3 R4 R5 R6 R7 R8 1R Ir 3 0 Ph P1 H HH H H H H H 310 Ir 3 0 Ph P1 H CF₃ H H H H H H 238 Ir 3 0 Ph P1 H F H HH H H H 242 Ir 3 0 Ph P1 F H F H H H H H 384 Ir 3 0 Ph P1 H CF₃ F H H HH H

COMPARATIVE EXAMPLE 5

[0147] A device was prepared in the same manner as in Example 8 exceptfor using the metal coordination compound (1R) shown in Table 4 in aweight ratio of 6 wt. %.

COMPARATIVE EXAMPLE 6

[0148] A device was prepared in the same manner as in Example 8 exceptfor using the metal coordination compound (1R) shown in Table 4 in aweight ratio of 8 wt. %.

[0149] Each device of Examples 10 -12 and Comparative Examples 4 -6 wassupplied with an electric field of 12 volts/100 nm with the ITO side asthe anode and the Al side as the cathode to measure a currentefficiency.

[0150] The results of devices using the respective compounds are shownin Table 5. As is understood from the results shown in Table 5, theconcentration giving a maximum current efficiency of ComparativeCompound 1R was clearly between 3% and 8%, whereas Example Compound No.310 provided with a substituent exhibited an increase in currentefficiency even at 8%. TABLE 5 <Comparison of current efficiency>Concentration Current Eff. Example Compound No. (wt. %) (cd/A) 10 310 32 11 310 6 2.4 12 310 8 2.7 Comp. 4 1R 3 15 Comp. 5 1R 6 19 Comp. 6 1R 817

[0151] Each device of Examples 13 -15 and Comparative Examples 4 -6 wassupplied with a voltage of 12 volts/100 nm with the ITO side as theanode and the A1 side as the cathode to measure an (electric) powerefficiency.

[0152] The results of the devices using the respective compounds areshown in Table 6. As is understood from the results shown in Table 6,the concentration giving a maximum power efficiency of the ComparativeCompound IR was between 3% and 8%, whereas Example Compound (238)provided with a substituent showed an increase in maximum efficiencyeven at a concentration of 8%. TABLE 6 <Comparison of power efficiency>Compound Concentration Power efficiency Example No. (wt. %) (lm/W) 13238 3 5.4 14 238 6 6 15 238 8 6.2 15A 238 11  6.5 15B 238 13  6.3 Comp.4 1R 3 5.7 Comp. 5 1R 6 6.2 Comp. 6 1R 8 6

[0153] Each device of Examples 16 -18 and Comparative Examples 4 -6 wassupplied with a voltage of 12 volts/100 nm with the ITO side as theanode and the Al side as the cathode to measure an external quantumefficiency, which was evaluated in terms of a ratio of luminance(1m)/current (mA) based on a value of current passing through the deviceby using a micro-current passing through the device by using amicro-current meter (“4140B”, made by Hewlett-Packard Corp.) and a valueof luminance measured by “BM7” (made by Topcon K.K.).

[0154] The results of the devices using the respective compounds areshown in Table 7. As is understood from the results shown in Table 7,the concentration giving a maximum external quantum efficiency of theComparative Compound 1R was between 3% and 8%, whereas Example Compound(242) provided with a substituent showed an increase in maximumefficiency even at a concentration of 8%. TABLE 7 <Comparison ofexternal quantum efficiency> Compound Concentration Ext. quantum ExampleNo. (wt. %) efficiency 16 242 3 3 17 242 6 4 18 242 8 4.2 Comp. 4 1R 3 7Comp. 5 1R 6 8 Comp. 6 1R 8 7.6

[0155] Each device of Examples 19 -21 and Comparative Examples 4 -6 wassupplied with a voltage of 12 volts/100 nm with the ITO side as theanode and the Al side as the cathode to measure an (electric) powerefficiency.

[0156] The results of the devices using the respective compounds areshown in Table 8. As is understood from the results shown in Table 8,the concentration giving a maximum power efficiency of the ComparativeCompound 1R was between 3% and 8%, whereas Example Compound (384)provided with a substituent showed an increase in maximum efficiencyeven at a concentration of 8%. TABLE 8 <Comparison of power efficiency>Compound Concentration Power efficiency Example No. (wt. %) (lm/W) 19384 3 2 20 384 6 2.3 21 384 8 2.6 Comp. 4 1R 3 5.7 Comp. 5 1R 6 6.2Comp. 6 1R 8 6

EXAMPLE 22

[0157] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (777) synthesized in Example 6in a weight ratio of 1 wt. %.

EXAMPLE 23

[0158] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (777) synthesized in Example 6in a weight ratio of 6 wt. %.

EXAMPLE 24

[0159] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (777) synthesized in Example 6in a weight ratio of 8 wt. %.

COMPARATIVE EXAMPLE 7

[0160] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (777R) shown in Table 9 below ina weight ratio of 1 wt. %. TABLE 9 A- A- A- A- B- B- B- B- No M m n A BR1 R2 R3 R4 R5 R6 R7 R8 777R Ir 3 0 Pe P1 H H H H H H H H 777 Ir 3 0 PeP1 H H H H H H CF₃ H

COMPARATIVE EXAMPLE 8

[0161] A device was prepared in the same manner as in Example 8 exceptfor using the metal coordination compound (777R) shown in Table 9 in aweight ratio of 6 wt. %.

COMPARATIVE EXAMPLE 9

[0162] A device was prepared in the same manner as in Example 8 exceptfor using the metal coordination compound (777R) shown in Table 9 in aweight ratio of 8 wt. %.

[0163] Each device of Examples 22 -25 and Comparative Examples 7 -9 wassupplied with a voltage of 12 volts/100 nm with the ITO side as theanode and the Al side as the cathode to measure an (electric) powerefficiency.

[0164] The results of the devices using the respective compounds areshown in Table 10. As is understood from the results shown in Table 6,the concentration giving a maximum power efficiency of ComparativeCompound 777R was between 1% and 8%, whereas Example Compound (777)provided with a substituent showed an increase in maximum efficiency upto a concentration of 8%. TABLE 10 <Comparison of maximum powerefficiency> Compound Concentration Power efficiency Example No. (wt. %)(lm/W) 22 777 1 0.04 23 777 6 0.12 24 777 8 0.15 Comp. 7 777R 1 0.08Comp. 8 777R 6 0.15 Comp. 9 777R 8 0.13

EXAMPLE 25

[0165] A device was prepared in the same manner as in Example 8 exceptfor using a metal coordination compound (472) synthesized in Example 7in a weight ratio of 3 wt. %.

EXAMPLE 26

[0166] A device was prepared in the same manner as in Example 1 exceptfor using a metal coordination compound (472) synthesized in Example 7in a weight ratio of 6 wt. %.

COMPARATIVE EXAMPLE 10

[0167] A device was prepared in the same manner as in Example 1 exceptfor using a metal coordination compound (472R) shown below in a weightratio of 3 wt. %.

COMPARATIVE EXAMPLE 11

[0168] A device was prepared in the same manner as in Example 1 exceptfor using the above metal coordination compound (472R) in a weight ratioof 6 wt. %.

COMPARATIVE EXAMPLE 12

[0169] A device was prepared in the same manner as in Example 1 exceptfor using the above metal coordination compound (472R) in a weight ratioof 8 wt. %.

[0170] Each device of Examples 25-27 and Comparative Examples 10-12 wassupplied with an electric field of 12 volts/100 nm with the ITO side asthe anode and the Al side as the cathode to measure a power efficiency.

[0171] In order to remove factors for device deterioration due to oxygenor water, the above-measurement was performed in a dry nitrogen flowafter taking the device out of the vacuum chamber.

[0172] The results of devices using the respective compounds are shownin Table 11. As is understood from the results shown in Table 11, theconcentration giving a maximum power efficiency of Comparative Compound1R was clearly between 3% and 8%, whereas Example Compound (384)provided with a substituent exhibited an increase in power efficiencyeven at a concentration of 8%. TABLE 11 <Comparison of maximum powerefficiency> Compound Concentration Power efficiency Example No. (wt. %)(lm/W) 25 472 3 5.6 26 472 6 6.3 27 472 8 6.5 Comp. 10 472R 3 5.4 Comp.11 472R 6 6 Comp. 12 472R 8 5.8

EXAMPLE 28

[0173]

[0174] In a 200 ml-three-necked flask, 3.50 g (25.0 mmol) of4-fluorophenylboronic acid, 3.95 g (25.0 mmol) of 1-bromopyridine, 25 mlof toluene, 12.5 ml of ethanol and 25 ml of 2M-sodium carbonate aqueoussolution, were placed and stirred at room temperature under a nitrogenstream, followed by addition of 0.98 g (0.85 mmol) oftetrakis(triphenylphosphine)palladium (0). Thereafter, the system wasrefluxed under stirring and nitrogen stream for 8 hours. Aftercompletion of the reaction, the reaction product was cooled andextracted by adding cold water and toluene. The organic layer was washedwith saline water and dried on magnesium sulfate, followed by removal ofthe solvent under a reduced pressure to provide dry solid. The residuewas purified by silica gel column chromatography (eluent:chloroform/methanol=10/1) to obtain 3.24 g (yield=75%) of Compound G.

[0175] In a 200 ml-three-necked, 0.881 g (2.5 mmol) of iridium (III)chloride trihydrate, 0.953 g (5.5 mmol), 75 ml of ethoxyethanol and 25ml of water were placed and stirred for 30 min. at room temperatureunder nitrogen stream, followed by 24 hours of reflux under stirring.The reaction product was cooled to room temperature, and the precipitatewas recovered by precipitation and washed successively with water,ethanol and acetone. After being dried at room temperature under areduced pressure, 1.32 g (yield: 92%) of yellow powdery Compound H wasobtained.

[0176] In a 200 mi-three-necked flask, 70 ml of ethoxyethanol, 0.80 g(0.7 mmol) of Compound H, 0.22 g (2.10 mmol) of acetylacetone and 1.04 g(9.91 mmol) of sodium carbonate, were placed and stirred for I hour atroom temperature under a nitrogen stream, followed by 15 hours of reflux under stirring. The reaction product was cooled with ice, and theprecipitate was filtered out and washed with water. The precipitate waspurified by silica gel chromatography (eluent: chloroform/methanol=30/1)to obtain 0.63 g (yield: 71%) of yellow powdery Compound I (ExampleCompound No. 489). A toluene solution of the compound exhibited aluminescence spectrum showing λmax=499 nm. Further, according toMALDI-TOF MS, M⁺=638.7 of the compound was confirmed.

[0177] In a 100 ml-three-necked flask, 0.21 g (1.2 mmol) of Compound G,0.32 g (0.5 mmol) of Compound I and 25 ml of glycerol, were placed andstirred for 8 hours around 180° C. under a nitrogen stream. The reactionproduct was cooled to room temperature and poured into 170 ml of1N-hydrochloric acid. The precipitate was filtered out and washed withwater, followed by drying for 5 hours at 100° C. under a reducedpressure. The precipitate was purified by silica gel columnchromatography with chloroform as the eluent to obtain 0.22 g (yield:63%) of yellow powdery Example Compound No. 239. A toluene solution ofthe compound exhibited a luminescence spectrum showing λmax=490 nm, andM⁺=708.8 of the compound was confirmed by MALDI-TOF MS.

EXAMPLE 29

[0178] Example Compound No. 535 was synthesized through a similarprocess as in Example 7.

[0179] Luminescence of toluene solution: λmax=525 nm MALDI-TOF MS:M⁺=671.1

EXAMPLE 30

[0180] Example Compound No. 243 was synthesized through a similarprocess as in Example 28.

[0181] Luminescence of toluene solution: λmax=518 nm MALDI-TOF MS:M⁺=762.7

EXAMPLE 31

[0182] Example Compound No. 511 was synthesized through a similarprocess as in Example 7.

[0183] Luminescence of toluene solution: λmax=514 nm MALDI-TOF MS:M⁺=628.1

EXAMPLE 32

[0184] Example Compound No. 56 was synthesized through a similar processas in Example 28.

[0185] Luminescence of toluene solution: λmax=505 nm MALDI-TOF MS:M⁺=697.2

EXAMPLE 33 Example Compound No. 389 was synthesized through a similarprocess as in Example 1.

[0186] Luminescence of toluene solution: λmax=503 nm

EXAMPLE 34

[0187] Example Compound No. 390 was synthesized through a similarprocess as in Example 1.

[0188] Luminescence of toluene solution: λmax=507 nm

EXAMPLE 35

[0189] Example Compound No. 312 was synthesized through a similarprocess as in Example 1.

[0190] The Luminescence of toluene solution exhibited two peaks at 458nm and 488 nm.

EXAMPLE 36

[0191] Example Compound No. 312 is synthesized through a similar processas in Example 1.

EXAMPLE 37)

[0192] Example Compound No. 314 is synthesized through a similar processas in Example 1.

EXAMPLE 38

[0193] Example Compound No. 388 is synthesized through a similar processas in Example 1.

EXAMPLE 39

[0194] Example Compound No. 392 is synthesized through a similar processas in Example 1.

EXAMPLE 40

[0195] Example Compound Nos. 274, 346, 358, 393 and 396 can besynthesized through a similar process except for changing the startingmaterial.

EXAMPLE 41

[0196] Hereinbelow, two examples of display apparatus are described.First, an example of preparation of a picture display apparatus havingan XY-matrix structure is described with reference to FIG. 2.

[0197] On a glass substrate 21 measuring 150 mm-length, 150 mm-width and1.1 mm-thickness, a ca. 100 nm-thick ITO film was formed by sputteringand patterned into 100 lines of 100 μm-wide transparent matrixelectrodes (anode side) with a spacing of 40 μm as simple matrixelectrodes. Then, a four-layered organic compound layer 23 was formedthereon including a luminescence layer 12 containing one of thecompounds synthesized in Examples 1-7 as a guest compound.

[0198] Then, 100 lines of 100 μm-wide metal electrodes 24 were formedwith a spacing of 40 μm by mask vacuum deposition so as to beperpendicular to the transparent electrodes by vacuum deposition at avacuum of 2×10⁻⁵ Torr. The metal electrodes were formed as a laminationof 10 nm-thick layer of Al/Li alloy (Li: 1.3 wt. %) and then 150nm-thick layer of Al.

[0199] The thus-obtained 100×100-simple matrix-type organic EL deviceswere subjected to a simple matrix drive in a glove box filled withnitrogen at voltages of 7 volts to 13 volts by using a scanning signalof 10 volts and data signals of ±3 volts as shown in FIG. 3. As a resultof an interlaced drive at a frame frequency of 30 Hz, luminescencepictures were confirmed for the respective devices.

[0200] As a picture display apparatus, the high-efficiency luminescencedevice of the present invention allows a light-weight flat panel displaywith economized energy consumption and high-recognizability. As aprinter light source, the luminescence devices of the present inventionmay be arranged in a line and disposed in proximity to thephotosensitive drum, to provide a line shutter wherein the respectivedevices are driven independently from each other to effect prescribedexposure on the photosensitive drum. On the other hand, the energyconsumption economization effect is expected in application as anillumination device or a backlight for a liquid crystal displayapparatus.

[0201] For another application to a picture display device, it isparticularly advantageous to form an active matrix-type picture displaydevice equipped with thin film transistors (TFTs) instead of theabove-mentioned XY-matrix wiring. Hereinbelow, an active matrix-typepicture display device according to the present invention will bedescribed with reference to FIGS. 4 to 6.

[0202]FIG. 4 is a schematic plan view of such a panel. Circumferentiallyoutside the panel are disposed a drive circuit comprising a power supplysource and a scanning signal driver, and a data signal driver as adisplay signal input means (called a picture data supply means, whichare respectively connected to current supply lines, X-direction scanninglines called gate lines and Y-direction lines called data lines. Thescanning signal driver sequentially selects the gate scanning lines, andin synchronism therewith, picture signals are supplied from the datasignal driver. Display pixels are disposed at intersections of the gatescanning lines and the data lines.

[0203] Next, a pixel circuit operation is described with reference to anequivalent circuit. When a selection signal is applied to a gateselection line, TFT1 is turned on so that a data signal is supplied froma data signal line to a capacitor Cadd, thereby determining the gatepotential of TFT2, whereby a current is supplied to an organicluminescence device (EL) disposed at each pixel through a current supplyline depending on the gate potential of TFT2. The gate potential of TFT2is held at Cadd during one frame period, so that the current continuallyflows from the current supply line to the EL device during the period.As a result, luminescence is retained during one frame period.

[0204]FIG. 6 is a schematic view illustrating a sectional structure of aTFT used in this Example. On a glass substrate, a polysilicone p-Silayer is formed, and the channel, drain and source regions are dopedwith necessary impurities, respectively. Thereon, gate electrodes areformed via a gate. insulating film, and drain electrodes and sourceelectrodes connected to the drain regions and source regions,respectively, are formed. In this instance, the drain electrodes andtransparent pixel electrodes (ITO) are connected through contact holesbored in an intervening insulating film.

[0205] The active device used in the present invention need not beparticularly restricted, and can also be a single-crystal silicon TFT,an amorphous silicon a-Si TFT, etc.

[0206] On the pixel electrodes, plural layers or a single layer oforganic luminescence layer may be disposed and metal electrodes ascathode are sequentially laminated to provide an active-type organicluminescence device.

[0207] [INDUSTRIAL APPLICABILITY]

[0208] As described above, a substituted metal coordination compoundhaving a high phosphorescence efficiency and a short phosphorescencelife can be used in a luminescence layer at a high concentrationrelative to the host material while preventing concentration extinction.As a result, according to the present invention, it is possible toobtain an excellent luminescence device showing high luminescenceefficiency. The luminescence device of the present invention is alsoexcellent as a display device.

1. An organic luminescence device, comprising: a pair of electrodes eachdisposed on a substrate, and at least one luminescence layer comprisingan organic compound disposed between the electrodes; wherein theluminescence layer comprises a non-luminescent first organic compoundand a phosphorescent second organic compound represented by formula (1)shown below, and the second organic compound is present at aconcentration of at least 8 wt. % in the luminescence layer:ML_(m)L′_(n)  (1), wherein M is a metal atom of Ir, Pt, Rh or Pd; L andL′ are mutually different bidentate ligands; m is 1, 2 or 3; n is 0, 1or 2 with the proviso that m+n is 2 or 3; a partial structure ML_(m) isrepresented by formula (2) shown below and a partial structure ML′_(n)is represented by formula (3), (4) or (5) shown below:

wherein N and C are nitrogen and carbon atoms, respectively; A and A′are respectively a cyclic group capable of having a substituent andbonded to the metal atom M via the carbon atom; B, B′ and B″ arerespectively a cyclic group represented by a formula of (6)-(14) shownbelow capable of having a substituent and connected to the metal atom Mvia the nitrogen atom:

{wherein the substituent is selected from a halogen atom, a cyano group,a nitro group, a trialkylsilyl group (of which the alkyl groups areindependently a linear or branched alkyl group having 1 to 8 carbonatoms), a linear or branched alkyl group having 1 to 20 carbon atoms (ofwhich the alkyl group can include one or non-neighboring two or moremethylene groups that can be replaced with —O—, —S—, —CO—, —CO—O—,—O—CO—, —CH═CH— or —C≡C— and the alkyl group can include a hydrogen atomthat can be replaced with a fluorine atom), or an aromatic cyclic groupcapable of having a substituent (of which the substituent is selectedfrom a halogen atom, a cyano group, a nitro group, a linear or branchedalkyl group having 1 to 20 carbon atoms (of which the alkyl group caninclude one or non-neighboring two or more methylene groups that can bereplaced with —O—, —S—, —CO—, —CO—O—, —O—CO—, —CH═CH— or —C≡C— and thealkyl group can include a hydrogen atom that can be replaced with afluorine atom)}; A and B, and A′ and B′ are respectively bonded to eachother via a covalent bond; E and G are independently a linear orbranched alkyl group having 1 to 20 carbon atoms (of which the alkylgroup can include a hydrogen atom that can be optionally replaced with afluorine atom), or an aromatic cyclic group capable of having asubstituent (of which the substituent is selected from a halogen atom, acyano group, a nitro group, a trialkylsilyl group (of which the alkylgroups are independently a linear or branched alkyl group having 1 to 8carbon atoms), a linear or branched alkyl group having 1 to 20 carbonatoms (of which the alkyl group can include one or non-neighboring twoor more methylene groups that can be replaced with —O—, —S—, —CO—,—CO—O—, —O—CO—, —CH═CH— or —C≡C— and the alkyl group can include ahydrogen atom that can be replaced with a fluorine atom)}, J is ahydrogen atom, a halogen atom, a linear or branched alkyl group having 1to 20 carbon atoms (of which the alkyl group can include a hydrogen atomthat can be optionally replaced with a fluorine atom), or an aromaticcyclic group capable of having a substituent {of which the substituentis selected from a halogen atom, a cyano group, a nitro group, atrialkylsilyl group (of which the alkyl groups are independently alinear or branched alkyl group having 1 to 8 carbon atoms), or a linearor branched alkyl group having 1 to 20 carbon atoms (of which the alkylgroup can include one or non-neighboring two or more methylene groupsthat can be replaced with —O—, —S—, —CO—, —CO—O—, —O—CO—, —CH═CH— or—C≡C— and the alkyl group can include a hydrogen atom that can bereplaced with a fluorine atom)}; wherein the compound represented by theformula (1) includes at least one cyclic group having a substituent. 2.An organic luminescence device according to claim 1, comprising: a pairof electrodes each disposed on a substrate, and at least oneluminescence layer comprising an organic compound disposed between theelectrodes; wherein the luminescence layer comprises a non-luminescentfirst organic compound and a phosphorescent second organic compoundrepresented by the above-mentioned formula (1), and the second organiccompound is present at a concentration in the luminescence layer that ishigher than a concentration at which an cyclic group represented by theformula (1) but containing no substituent in any of the cyclic groups Aand A′ or the cyclic groups B and B′ exhibits a maximum luminescencecharacteristic.
 3. An organic luminescence device according to claim 1,comprising: a pair of electrodes each disposed on a substrate, and atleast one luminescence layer comprising an organic compound disposedbetween the electrodes; wherein the luminescence layer comprises anon-luminescent first organic compound and a phosphorescent secondorganic compound represented by the above-mentioned formula (1), and thesecond organic compound is present at a prescribed concentration of atleast 8 wt. % in the luminescence layer providing a maximum luminescencecharacteristic.
 4. An organic luminescence device according to claim 1,wherein the partial structure ML′_(n) in the formula (1) is representedby the formula (3).
 5. An organic luminescence device according to claim1, wherein the partial structure ML′_(n) in the formula (1) isrepresented by the formula (4).
 6. An organic luminescence deviceaccording to claim 1, wherein the partial structure ML′_(n) in theformula (1) is represented by the formula (5).
 7. An organicluminescence device according to claim 1, wherein n in the formula (1)is
 0. 8. An organic luminescence device according to claim 1, whereinthe substituent of the compound of the formula (1) is fluorine.
 9. Anorganic luminescence device according to claim 1, wherein thesubstituent of the compound of the formula (1) is a trifluoromethylgroup.
 10. An organic luminescence device according to claim 1, whereinthe substituent of the compound of the formula (1) is an alkyl group.11. An organic luminescence device according to claim 2, wherein saidmaximum luminescence characteristic is a maximum luminescence luminance.12. An organic luminescence device according to claim 2, wherein saidmaximum luminescence characteristic is a maximum current.
 13. An organicluminescence device according to claim 2, wherein said maximumluminescence characteristic is an external luminescence efficiency. 14.An organic luminescence device according to claim 2, wherein saidmaximum luminescence characteristic is a ratio of luminescenceflux/power consumption obtained by dividing a luminescence flux by apower consumption.
 15. An organic luminescence device according to claim1, wherein phosphorescence is emitted from the luminescence layer byapplying a voltage between the electrodes.
 16. A picture displayapparatus, comprising an organic luminescence device according to claim1, and a drive circuit for supplying display data.